JP2000063766A - Adhesive for optical disk - Google Patents
Adhesive for optical diskInfo
- Publication number
- JP2000063766A JP2000063766A JP10233997A JP23399798A JP2000063766A JP 2000063766 A JP2000063766 A JP 2000063766A JP 10233997 A JP10233997 A JP 10233997A JP 23399798 A JP23399798 A JP 23399798A JP 2000063766 A JP2000063766 A JP 2000063766A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylate
- component
- adhesive
- glycol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 36
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 34
- 230000003287 optical effect Effects 0.000 title claims abstract description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 123
- -1 polyol compound Chemical class 0.000 claims abstract description 56
- 229920005862 polyol Polymers 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
- 150000001875 compounds Chemical group 0.000 claims abstract description 17
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims abstract description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 8
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 8
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims abstract description 4
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 4
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 abstract description 23
- 239000010931 gold Substances 0.000 abstract description 11
- 239000011347 resin Substances 0.000 abstract description 10
- 229920005989 resin Polymers 0.000 abstract description 10
- 229910052782 aluminium Inorganic materials 0.000 abstract description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 9
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052737 gold Inorganic materials 0.000 abstract description 9
- 229920000515 polycarbonate Polymers 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 46
- 239000000203 mixture Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 31
- 150000003077 polyols Chemical class 0.000 description 25
- 239000000758 substrate Substances 0.000 description 22
- 239000000126 substance Substances 0.000 description 20
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 19
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 19
- 239000004721 Polyphenylene oxide Substances 0.000 description 15
- 150000002009 diols Chemical class 0.000 description 15
- 229920000570 polyether Polymers 0.000 description 15
- 125000002947 alkylene group Chemical group 0.000 description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 11
- 229940113165 trimethylolpropane Drugs 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 7
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 6
- 229920000298 Cellophane Polymers 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000013065 commercial product Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 238000004544 sputter deposition Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000003712 anti-aging effect Effects 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 229940042596 viscoat Drugs 0.000 description 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001923 cyclic compounds Chemical class 0.000 description 4
- 230000001678 irradiating effect Effects 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 3
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 239000004632 polycaprolactone Substances 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- MLKIVXXYTZKNMI-UHFFFAOYSA-N 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one Chemical compound CCCCCCCCCCCCC1=CC=C(C(=O)C(C)(C)O)C=C1 MLKIVXXYTZKNMI-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- RSROEZYGRKHVMN-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;oxirane Chemical compound C1CO1.CCC(CO)(CO)CO RSROEZYGRKHVMN-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- SDQROPCSKIYYAV-UHFFFAOYSA-N 2-methyloctane-1,8-diol Chemical compound OCC(C)CCCCCCO SDQROPCSKIYYAV-UHFFFAOYSA-N 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- DVNPFNZTPMWRAX-UHFFFAOYSA-N 2-triethoxysilylethanethiol Chemical compound CCO[Si](CCS)(OCC)OCC DVNPFNZTPMWRAX-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 239000004831 Hot glue Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000004205 dimethyl polysiloxane Chemical class 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 2
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Chemical class 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 150000007519 polyprotic acids Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 2
- 229950006800 prenderol Drugs 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/256—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers improving adhesion between layers
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
- G11B7/2534—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/258—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers
- G11B7/2585—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers based on aluminium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/913—Material designed to be responsive to temperature, light, moisture
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/146—Laser beam
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/21—Circular sheet or circular blank
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、光硬化型の光ディ
スク用接着剤に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photocurable adhesive for optical disks.
【0002】[0002]
【従来の技術】近年、コンピューター装置技術、コンピ
ューターソフトウエア技術、通信技術等をはじめとする
情報技術の発展により、より多くの情報を高速に伝達す
ることが可能となってきている。これに伴いより多くの
情報を高密度に記録することができる記録媒体が望まれ
開発が進められつつある。このような高密度記録媒体と
してDVD(デジタルビデオディスクまたはデジタルバ
ーサタイルディスクと称する)が次世代の汎用の記録媒
体として開発されている。DVDは従来のCD(コンパ
クトディスク)と異なり、2枚のディスクを張り合わせ
て製造されるために張り合わせのための接着剤が必要と
なり、ホットメルト接着剤、熱硬化型接着剤、嫌気硬化
型接着剤等を用いる試みがなされている。しかし、ホッ
トメルト接着剤では熱安定性や耐候性が十分ではなく高
温環境下で軟化するため接着強度が低下して張り合わせ
たディスクが剥がれたり変形したりする問題がある。ま
た、透明性が高くないため記録膜として半透過膜を有す
る二層構造のDVDでは使用が困難である。熱硬化型接
着剤では硬化するときの熱によりディスクを構成する基
材が変形したり、硬化に要する時間が長い等の問題があ
る。嫌気型接着剤も硬化に時間がかかるため生産性が低
いという問題がある。このような問題を解決する方法と
して光硬化型の接着剤が提案されている。例えば、特開
昭61−142545号公報および特開平6−8946
2号公報にはウレタンアクリレートを主成分とする紫外
線硬化型樹脂接着剤が開示されている。2. Description of the Related Art In recent years, with the development of information technology such as computer device technology, computer software technology, communication technology, etc., more information can be transmitted at high speed. Along with this, a recording medium capable of recording more information with high density is desired and is being developed. As such a high-density recording medium, a DVD (called a digital video disc or a digital versatile disc) has been developed as a next-generation general-purpose recording medium. Unlike conventional CDs (compact discs), DVDs are manufactured by laminating two discs together, and therefore an adhesive for laminating is required. Hot melt adhesives, thermosetting adhesives, anaerobic curing adhesives Attempts have been made to use the above. However, the hot melt adhesive has insufficient thermal stability and weather resistance and softens in a high temperature environment, so that there is a problem that the adhesive strength is lowered and the bonded disks are peeled or deformed. Moreover, since the transparency is not high, it is difficult to use a DVD having a double-layer structure having a semi-transmissive film as a recording film. The thermosetting adhesive has the problems that the base material forming the disk is deformed by the heat at the time of hardening and that the time required for hardening is long. The anaerobic adhesive also has a problem of low productivity because it takes time to cure. A photocurable adhesive has been proposed as a method for solving such a problem. For example, JP-A-61-242545 and JP-A-6-8946.
No. 2 discloses an ultraviolet-curable resin adhesive containing urethane acrylate as a main component.
【0003】[0003]
【発明が解決しようとする課題】しかしながら、これら
の紫外線硬化型樹脂接着剤も、ディスクを構成するポリ
カーボネートなどの樹脂、反射膜を形成するアルミニウ
ム、半透過膜を形成する金などとの接着性や、耐湿熱性
等の点で未だ充分満足できるものではなかった。従っ
て、本発明が解決しようとする課題は、光ディスク用の
紫外線硬化型樹脂接着剤であって、従来のものよりもポ
リカーボネートなどの樹脂、アルミニウム、金などとの
優れた接着性、および優れた耐湿熱性を有する光ディス
ク用接着剤を提供することにある。However, these UV-curable resin adhesives also have adhesiveness with resins such as polycarbonate forming a disk, aluminum forming a reflective film, and gold forming a semi-transmissive film. However, it was still not sufficiently satisfactory in terms of moist heat resistance. Therefore, the problem to be solved by the present invention is an ultraviolet-curable resin adhesive for optical discs, which has superior adhesiveness to resins such as polycarbonate, aluminum, gold, etc. and superior moisture resistance to conventional ones. It is to provide an adhesive for an optical disk having heat.
【0004】[0004]
【課題を解決するための手段】本発明者らは、鋭意検討
した結果、以下に示す特定の光ディスク用接着剤により
前記課題を解決できることを見いだした。As a result of intensive studies, the present inventors have found that the above-mentioned problems can be solved by the following specific optical disk adhesive.
【0005】すなわち、本発明は、次の成分(A)、
(B)および(C);
(A)ポリオール化合物、ポリイソシアネート化合物お
よび水酸基含有(メタ)アクリレート化合物を反応させ
て得られるウレタン(メタ)アクリレート、(B)ヒド
ロキシアルキル(メタ)アクリレート、(C)2,2−
ジメトキシ−1,2−ジフェニルエタン−1−オン、2
−ヒドロキシ−2−メチル−1−フェニル−プロパン−
1−オンおよび/または1−ヒドロキシ−シクロヘキシ
ルフェニルケトンを含有する光ディスク用接着剤を提供
するものである。That is, the present invention provides the following component (A),
(B) and (C); (A) a urethane compound (meth) acrylate obtained by reacting a polyol compound, a polyisocyanate compound and a hydroxyl group-containing (meth) acrylate compound, (B) a hydroxyalkyl (meth) acrylate, (C). 2,2-
Dimethoxy-1,2-diphenylethan-1-one, 2
-Hydroxy-2-methyl-1-phenyl-propane-
The present invention provides an adhesive for an optical disc containing 1-one and / or 1-hydroxy-cyclohexyl phenyl ketone.
【0006】[0006]
【発明の実施の形態】成分(A)のウレタン(メタ)ア
クリレートは、前記のとおりポリオール化合物、ポリイ
ソシアネート化合物および水酸基含有(メタ)アクリレ
ート化合物を反応させて得られる。BEST MODE FOR CARRYING OUT THE INVENTION The urethane (meth) acrylate as the component (A) is obtained by reacting a polyol compound, a polyisocyanate compound and a hydroxyl group-containing (meth) acrylate compound as described above.
【0007】用いられるポリオール化合物としては、ポ
リエーテルポリオール、ポリエステルポリオール、ポリ
カーボネートポリオール、ポリカプロラクトンポリオー
ル、分子中に2個以上の水酸基を有する脂肪族炭化水
素、分子中に2個以上の水酸基を有する脂環式炭化水
素、分子中に2個以上の水酸基を有する不飽和炭化水素
等が用いられる。これらのポリオールは単独で用いるこ
とも、2種類以上併用することもできる。The polyol compounds used include polyether polyols, polyester polyols, polycarbonate polyols, polycaprolactone polyols, aliphatic hydrocarbons having two or more hydroxyl groups in the molecule, and fats having two or more hydroxyl groups in the molecule. Cyclic hydrocarbons, unsaturated hydrocarbons having two or more hydroxyl groups in the molecule, and the like are used. These polyols can be used alone or in combination of two or more kinds.
【0008】上記ポリエーテルポリオールとしては、脂
肪族ポリエーテルポリオール、脂環式ポリエーテルポリ
オール、芳香族ポリエーテルポリオールを挙げることが
できる。Examples of the above polyether polyols include aliphatic polyether polyols, alicyclic polyether polyols and aromatic polyether polyols.
【0009】ここで、脂肪族ポリエーテルポリオールと
しては、例えばポリエチレングリコール、ポリプロピレ
ングリコール、ポリテトラメチレングリコール、ポリヘ
キサメチレングリコール、ポリヘプタメチレングリコー
ル、ポリデカメチレングリコール、ペンタエリスリトー
ル、ジペンタエリスリトール、トリメチロールプロパ
ン、およびトリメチロールプロパンのエチレンオキサイ
ド付加トリオール、トリメチロールプロパンのプロピレ
ンオキサイド付加トリオール、トリメチロールプロパン
のエチレンオキサイドとプロピレンオキサイド付加トリ
オール、ペンタエリスリトールのエチレンオキサイド付
加テトラオール、ジペンタエリスリトールのエチレンオ
キサイド付加ヘキサオール等のアルキレンオキサイド付
加ポリオール等の多価アルコール、あるいは2種類以上
のイオン重合性環状化合物を開環重合させて得られるポ
リエーテルポリオール等が挙げられる。Examples of the aliphatic polyether polyols include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyhexamethylene glycol, polyheptamethylene glycol, polydecamethylene glycol, pentaerythritol, dipentaerythritol and trimethylol. Propane and trimethylolpropane ethylene oxide adduct triol, trimethylol propane propylene oxide adduct triol, trimethylol propane ethylene oxide and propylene oxide adduct triol, pentaerythritol ethylene oxide adduct tetraol, dipentaerythritol ethylene oxide adduct hexa A large amount of alkylene oxide addition polyols such as oar Alcohols, or two or more kinds of polyether polyol obtained by ring-opening polymerization of ion-polymerizable cyclic compounds, and the like.
【0010】なお、イオン重合性環状化合物としては、
例えばエチレンオキシド、プロピレンオキシド、ブテン
−1−オキシド、イソブテンオキシド、3,3,−ビス
クロロメチルオキセタン、テトラヒドロフラン、2−メ
チルテトラヒドロフラン、ジオキサン、トリオキサン、
テトラオキサン、シクロヘキセンオキシド、スチレンオ
キシド、エピクロルヒドリン、グリシジルエーテル、ア
リルグリシジルエーテル、アリルグリシジルカーボネー
ト、ブタジエンモノオキシド、イソプレンモノオキシ
ド、ビニルオキセタン、ビニルテトラヒドロフラン、ビ
ニルシクロヘキセンオキシド、フェニルグリシジルエー
テル、ブチルグリシジルエーテル、安息香酸グリシジル
エステル等の環状エーテル類が挙げられる。上記二種類
以上のイオン重合性環状化合物の具体的な組み合わせと
しては、テトラヒドロフランとエチレンオキシド、テト
ラヒドロフランとプロピレンオキシド、テトラヒドロフ
ランと2−メチルテトラヒドロフラン、テトラヒドロフ
ランと3−メチルテトラヒドロフラン、エチレンオキシ
ドとプロピレンオキシド、ブテン−1−オキシドとエチ
レンオキシド、テトラヒドロフランとブテン−1−オキ
シドとエチレンオキシド等を挙げることができる。As the ionic polymerizable cyclic compound,
For example, ethylene oxide, propylene oxide, butene-1-oxide, isobutene oxide, 3,3, -bischloromethyloxetane, tetrahydrofuran, 2-methyltetrahydrofuran, dioxane, trioxane,
Tetraoxane, cyclohexene oxide, styrene oxide, epichlorohydrin, glycidyl ether, allyl glycidyl ether, allyl glycidyl carbonate, butadiene monooxide, isoprene monoxide, vinyl oxetane, vinyl tetrahydrofuran, vinyl cyclohexene oxide, phenyl glycidyl ether, butyl glycidyl ether, glycidyl benzoate Examples include cyclic ethers such as esters. Specific combinations of the two or more types of ion-polymerizable cyclic compounds include tetrahydrofuran and ethylene oxide, tetrahydrofuran and propylene oxide, tetrahydrofuran and 2-methyltetrahydrofuran, tetrahydrofuran and 3-methyltetrahydrofuran, ethylene oxide and propylene oxide, butene-1-. Examples thereof include oxide and ethylene oxide, tetrahydrofuran, butene-1-oxide, and ethylene oxide.
【0011】また、上記イオン重合性環状化合物と、エ
チレンイミン等の環状イミン類、β−プロピオラクト
ン、グリコール酸ラクチド等の環状ラクトン酸、あるい
はジメチルシクロポリシロキサン類とを開環共重合させ
たポリエーテルポリオールを使用することもできる。Further, the above-mentioned ion-polymerizable cyclic compound was subjected to ring-opening copolymerization with cyclic imine such as ethyleneimine, cyclic lactone acid such as β-propiolactone and glycolic acid lactide, or dimethylcyclopolysiloxane. It is also possible to use polyether polyols.
【0012】脂環式ポリエーテルポリオールとしては、
例えば水添ビスフェノールAのアルキレンオキシド付加
ジオール、水添ビスフェノールFのアルキレンオキシド
付加ジオール、1,4−シクロヘキサンジオールのアル
キレンオキシド付加ジオール等が挙げられる。As the alicyclic polyether polyol,
Examples thereof include alkylene oxide addition diol of hydrogenated bisphenol A, alkylene oxide addition diol of hydrogenated bisphenol F, and alkylene oxide addition diol of 1,4-cyclohexanediol.
【0013】芳香族ポリエーテルポリオールとしては、
例えばビスフェノールAのアルキレンオキシド付加ジオ
ール、ビスフェノールFのアルキレンオキシド付加ジオ
ール、ハイドロキノンのアルキレンオキシド付加ジオー
ル、ナフトハイドロキノンのアルキレンオキシド付加ジ
オール、アントラハイドロキノンのアルキレンオキシド
付加ジオール等が挙げられる。As the aromatic polyether polyol,
Examples include alkylene oxide addition diol of bisphenol A, alkylene oxide addition diol of bisphenol F, alkylene oxide addition diol of hydroquinone, alkylene oxide addition diol of naphthohydroquinone, alkylene oxide addition diol of anthrahydroquinone, and the like.
【0014】上記ポリエーテルポリオールの市販品とし
ては、例えば脂肪族ポリエーテルポリオールとしては、
PTMG650、PTMG1000、PTMG2000
(以上、三菱化学(株)製)、PPG1000、EXE
NOL1020、EXENOL2020、EXENOL
3020、EXENOL4020(以上、旭硝子(株)
製)、PEG1000、ユニセーフDC1100、ユニ
セーフDC1800、ユニセーフDCB1100、ユニ
セーフDCB1800(以上、日本油脂(株))、PP
TG1000、PPTG2000、PPTG4000、
PTG400、PTG650、PTG2000、PTG
3000、PTGL1000、PTGL2000(以
上、保土谷化学(株)製)、Z−3001−4、Z−3
001−5、PBG2000、PBG2000B(以
上、第一工業製薬(株)製)、TMP30、PNT4グ
リコール、EDA P4、 EDA P8(以上、日本
乳化剤(株)製)、クオドロール(旭電化(株)製)が
挙げられる。芳香族ポリエーテルポリオールとしてはユ
ニオールDA400、DA700、DA1000、DB
400(以上、日本油脂(株)製)等を挙げることがで
きる。Commercially available products of the above polyether polyols include, for example, aliphatic polyether polyols.
PTMG650, PTMG1000, PTMG2000
(Made by Mitsubishi Chemical Corporation), PPG1000, EXE
NOL1020, EXENOL2020, EXENOL
3020, EXENOL 4020 (above, Asahi Glass Co., Ltd.
), PEG1000, Unisafe DC1100, Unisafe DC1800, Unisafe DCB1100, Unisafe DCB1800 (above, NOF Corporation), PP
TG1000, PPTG2000, PPTG4000,
PTG400, PTG650, PTG2000, PTG
3000, PTGL1000, PTGL2000 (above, Hodogaya Chemical Co., Ltd.), Z-3001-4, Z-3.
001-5, PBG2000, PBG2000B (all manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), TMP30, PNT4 glycol, EDA P4, EDA P8 (all manufactured by Nippon Emulsifier Co., Ltd.), quadrol (Made by Asahi Denka Co., Ltd.) Is mentioned. As the aromatic polyether polyol, Uniol DA400, DA700, DA1000, DB
400 (above, NOF Corporation make) etc. can be mentioned.
【0015】また、上記ポリエステルポリオールは、多
価アルコールと多塩基酸とを反応させて得られる。ここ
で、多価アルコールとしては、エチレングリコール、ポ
リエチレングリコール、プロピレングリコール、ポリプ
ロピレングリコール、テトラメチレングリコール、ポリ
テトラメチレングリコール、1,4−ブタンジオール、
1,5−ペンタンジオール、1,6−ヘキサンジオー
ル、1,7−ヘプタンジオール、1,8−オクタンジオ
ール、ネオペンチルグリコール、1,4−シクロヘキサ
ンジオール、1,4−シクロヘキサンジメタノール、
1,2−ビス(ヒドロキシエチル)シクロヘキサン、
2,2−ジエチル−1,3−プロパンジオール、3−メ
チル−1,5−ペンタンジオール、1,9−ノナンジオ
ール、2−メチル−1,8−オクタンジオール、グリセ
リン、トリメチロールプロパン、トリメチロールプロパ
ンのエチレンオキシド付加体、トリメチロールプロパン
のプロピレンオキシド付加体、トリメチロールプロパン
のエチレンオキシドとプロピレンオキシドの付加体、ソ
ルビトール、ペンタエリスリトール、ジペンタエリスリ
トール、アルキレンオキシド付加ポリオール等が挙げら
れる。また、多塩基酸としては、例えばフタル酸、イソ
フタル酸、テレフタル酸、マレイン酸、フマル酸、アジ
ピン酸、セバシン酸、等を挙げることができる。これら
のポリエステルポリオールの市販品としては、クラポー
ルP1010、クラポールP2010、PMIPA、P
KA−A、PKA−A2、PNA−2000(以上、ク
ラレ(株)製)等を使用することができる。Further, the polyester polyol is obtained by reacting a polyhydric alcohol with a polybasic acid. Here, as the polyhydric alcohol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1,4-butanediol,
1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, neopentyl glycol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol,
1,2-bis (hydroxyethyl) cyclohexane,
2,2-diethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 1,9-nonanediol, 2-methyl-1,8-octanediol, glycerin, trimethylolpropane, trimethylol Examples thereof include ethylene oxide adduct of propane, propylene oxide adduct of trimethylolpropane, adduct of ethylene oxide and propylene oxide of trimethylolpropane, sorbitol, pentaerythritol, dipentaerythritol, and alkylene oxide adduct polyol. Examples of polybasic acids include phthalic acid, isophthalic acid, terephthalic acid, maleic acid, fumaric acid, adipic acid and sebacic acid. Commercially available products of these polyester polyols include Clapol P1010, Clapol P2010, PMIPA, P
KA-A, PKA-A2, PNA-2000 (all manufactured by Kuraray Co., Ltd.) and the like can be used.
【0016】また、上記ポリカーボネートポリオールと
しては、例えば式(1)で示されるポリカーボネートジ
オールが挙げられる。Examples of the polycarbonate polyol include polycarbonate diol represented by the formula (1).
【0017】[0017]
【化1】 [Chemical 1]
【0018】(式中、R1 は炭素数2〜20のアルキレ
ン基、(ポリ)エチレングリコール残基、(ポリ)プロ
ピレングリコール残基、(ポリ)テトラメチレングリコ
ール残基を表し、mは1〜30の整数である。)(Wherein R 1 represents an alkylene group having 2 to 20 carbon atoms, a (poly) ethylene glycol residue, a (poly) propylene glycol residue, or a (poly) tetramethylene glycol residue, and m is 1 to It is an integer of 30.)
【0019】R1 の具体例としては、次の化合物から両
末端水酸基を除いた残基、すなわち1,4−ブタンジオ
ール、1,5−ペンタンジオール、ネオペンチルグリコ
ール、1,6−ヘキサンジオール、1,4−シクロヘキ
サンジメタノール、1、7−ヘプタンジオール、1,8
−オクタンジオール、1,9−ノナンジオール、エチレ
ングリコール、ジエチレングリコール、トリエチレング
リコール、テトラエチレングリコール、プロピレングリ
コール、ジプロピレングリコール、トリプロピレングリ
コール、テトラプロピレングリコール等から水酸基を除
いた残基が挙げられる。該ポリカーボネートポリオール
としては、市販品として、DN−980、DN−98
1、DN−982、DN−983(以上、日本ポリウレ
タン工業(株)製)、PC−8000(PPG社製)、
PNOC1000、PNOC2000、PMC100、
PMC2000(以上、(株)クラレ製)、プラクセル
CD−205、CD−208、CD−210、CD−
220、CD−205PL、CD−208PL、CD−
210PL、CD−220PL、CD−205HL、C
D−208HL、CD−210HL、CD−220H
L、CD−210T、CD−221T(以上、ダイセル
化学工業(株)製)等を使用することができる。Specific examples of R 1 are residues obtained by removing hydroxyl groups at both terminals from the following compounds: 1,4-butanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, 1,7-heptanediol, 1,8
-Octan diol, 1,9-nonane diol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, and the like may be mentioned residues obtained by removing a hydroxyl group. As the polycarbonate polyol, DN-980 and DN-98 are commercially available products.
1, DN-982, DN-983 (all manufactured by Nippon Polyurethane Industry Co., Ltd.), PC-8000 (manufactured by PPG),
PNOC1000, PNOC2000, PMC100,
PMC2000 (above, manufactured by Kuraray Co., Ltd.), Praxel CD-205, CD-208, CD-210, CD-
220, CD-205PL, CD-208PL, CD-
210PL, CD-220PL, CD-205HL, C
D-208HL, CD-210HL, CD-220H
L, CD-210T, CD-221T (above, Daicel Chemical Industries Ltd. make) etc. can be used.
【0020】上記ポリカプロラクトンポリオールとして
は、εーカプロラクトンを例えば、エチレングリコー
ル、ポリエチレングリコール、プロピレングリコール、
ポリプロピレングリコール、テトラメチレングリコー
ル、ポリテトラメチレングリコール、1,2−ポリブチ
レングリコール、1,6−ヘキサンジオール、ネオペン
チルグリコール、1,4−シクロヘキサンジメタノー
ル、1,4−ブタンジオール等のジオールに付加反応さ
せて得られるポリカプロラクトンジオールが挙げられ
る。これらの市販品としては、プラクセル 205、2
05AL、212、212AL、220、220AL
(以上、ダイセル化学工業(株)製)等を使用すること
ができる。As the above polycaprolactone polyol, ε-caprolactone is, for example, ethylene glycol, polyethylene glycol, propylene glycol,
Addition to diols such as polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1,2-polybutylene glycol, 1,6-hexanediol, neopentyl glycol, 1,4-cyclohexanedimethanol, 1,4-butanediol The polycaprolactone diol obtained by reacting is mentioned. These commercially available products include Praxel 205, 2
05AL, 212, 212AL, 220, 220AL
(These are manufactured by Daicel Chemical Industries, Ltd.) and the like can be used.
【0021】分子中に2個以上の水酸基を有する脂肪族
炭化水素としては、エチレングリコール、プロピレング
リコール、テトラメチレングリコール、1,4−ブタン
ジオール、1,5−ペンタンジオール、1,6−ヘキサ
ンジオール、1、7−ヘプタンジオール、1,8−オク
タンジオール、1,9−ノナンジオール、ネオペンチル
グリコール、2,2−ジエチル−1,3−プロパンジオ
ール、3−メチル−1,5−ペンタンジオール、2−メ
チル−1,8−オクタンジオール、ヒドロキシ末端水添
ポリブタジエン、グリセリン、トリメチロールプロパ
ン、ペンタエリスリトール、ソルビトール等が挙げられ
る。Examples of the aliphatic hydrocarbon having two or more hydroxyl groups in the molecule include ethylene glycol, propylene glycol, tetramethylene glycol, 1,4-butanediol, 1,5-pentanediol and 1,6-hexanediol. 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, neopentyl glycol, 2,2-diethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, Examples thereof include 2-methyl-1,8-octanediol, hydroxy-terminated hydrogenated polybutadiene, glycerin, trimethylolpropane, pentaerythritol, and sorbitol.
【0022】分子中に2個以上の水酸基を有する脂環式
炭化水素としては、例えば1,4−シクロヘキサンジオ
ール、1,4−シクロヘキサンジメタノール、1,2−
ビス(ヒドロキシエチル)シクロヘキサン、ジシクロペ
ンタジエンのジメチロール化合物、トリシクロデカンジ
メタノール等が挙げられる。Examples of the alicyclic hydrocarbon having two or more hydroxyl groups in the molecule include 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, 1,2-
Examples thereof include bis (hydroxyethyl) cyclohexane, a dimethylol compound of dicyclopentadiene, and tricyclodecane dimethanol.
【0023】分子中に2個以上の水酸基を有する不飽和
炭化水素としては、例えばヒドロキシ末端ポリブタジエ
ン、ヒドロキシ末端ポリイソプレン等が挙げられる。Examples of the unsaturated hydrocarbon having two or more hydroxyl groups in the molecule include hydroxy-terminated polybutadiene and hydroxy-terminated polyisoprene.
【0024】さらにまた、上記以外のポリオールとして
は、例えばβ−メチル−δ−バレロラクトンジオール、
ひまし油変性ジオール、ポリジメチルシロキサンの末端
ジオール化合物、ポリジメチルシロキサンカルビトール
変性ジオール等が挙げられる。Furthermore, as the polyol other than the above, for example, β-methyl-δ-valerolactone diol,
Examples thereof include castor oil-modified diols, polydimethylsiloxane terminal diol compounds, and polydimethylsiloxane carbitol-modified diols.
【0025】これらのポリオール化合物の好ましい数平
均分子量は50〜15000、特に好ましくは100〜
8000である。The number average molecular weight of these polyol compounds is preferably 50 to 15,000, particularly preferably 100 to 15,000.
It is 8000.
【0026】また、上記ポリイソシアネート化合物とし
てはジイソシアネート化合物が好ましく、例えば2,4
−トリレンジイソシアネート、2,6−トリレンジイソ
シアネート、1,3−キシリレンジイソシアネート、
1,4−キシリレンジイソシアネート、1,5−ナフタ
レンジイソシアネート、m−フェニレンジイソシアネー
ト、p−フェニレンジイソシアネート、3,3´−ジメ
チル−4,4´−ジフェニルメタンジイソシアネート、
4,4´−ジフェニルメタンジイソシアネート、3,3
´−ジメチルフェニレンジイソシアネート、4,4´−
ビフェニレンジイソシアネート、1,6−ヘキサンジイ
ソシアネート、イソホロンジイソシアネート、2,2,
4−トリメチルヘキサメチレンジイソシアネート、ビス
(2−イソシアネートエチル)フマレート、6−イソプ
ロピル−1,3−フェニルジイソシアネート、4−ジフ
ェニルプロパンジイソシアネート、リジンジイソシアネ
ート、水添ジフェニルメタンジイソシアネート、水添キ
シリレンジイソシアネート、テトラメチルキシリレンジ
イソシアネート等が挙げられる。これらのうち、特に
2,4−トリレンジイソシアネート、2,6−トリレン
ジイソシアネート、水添キシリレンジイソシアネート、
イソホロンジイソシアネート、水添ジフェニルメタンジ
イソシアネート等が好ましい。これらのジイソシアネー
トは単独または2種類以上を組み合わせて用いることが
できる。The polyisocyanate compound is preferably a diisocyanate compound, for example, 2,4
-Tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylylene diisocyanate,
1,4-xylylene diisocyanate, 1,5-naphthalene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 3,3′-dimethyl-4,4′-diphenylmethane diisocyanate,
4,4'-diphenylmethane diisocyanate, 3,3
′ -Dimethylphenylene diisocyanate, 4,4′-
Biphenylene diisocyanate, 1,6-hexane diisocyanate, isophorone diisocyanate, 2,2
4-trimethylhexamethylene diisocyanate, bis (2-isocyanate ethyl) fumarate, 6-isopropyl-1,3-phenyl diisocyanate, 4-diphenylpropane diisocyanate, lysine diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, tetramethylxylyl Examples include diisocyanate. Of these, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hydrogenated xylylene diisocyanate,
Isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate and the like are preferable. These diisocyanates can be used alone or in combination of two or more kinds.
【0027】水酸基含有(メタ)アクリレートはエステ
ル残基に水酸基を有する(メタ)アクリレートであり、
例えば2−ヒドロキシエチル(メタ)アクリレート、2
−ヒドロキシプロピル(メタ)アクリレート、4−ヒド
ロキシブチル(メタ)アクリレート、2−ヒドロキシ−
3−フェニルオキシプロピル(メタ)アクリレート、
1,4−ブタンジオールモノ(メタ)アクリレート、2
−ヒドロキシアルキル(メタ)アクリロイルホスフェー
ト、4−ヒドロキシシクロヘキシル(メタ)アクリレー
ト、1,6−ヘキサンジオールモノ(メタ)アクリレー
ト、ネオペンチルグリコールモノ(メタ)アクリレー
ト、トリメチロールプロパンジ(メタ)アクリレート、
トリメチロールエタンジ(メタ)アクリレート、ペンタ
エリスリトールトリ(メタ)アクリレート、ジペンタエ
リスリトールペンタ(メタ)アクリレート、あるいは下
記構造式(2)で表される(メタ)アクリレート等が挙
げられ、The hydroxyl group-containing (meth) acrylate is a (meth) acrylate having a hydroxyl group in the ester residue,
For example, 2-hydroxyethyl (meth) acrylate, 2
-Hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxy-
3-phenyloxypropyl (meth) acrylate,
1,4-butanediol mono (meth) acrylate, 2
-Hydroxyalkyl (meth) acryloyl phosphate, 4-hydroxycyclohexyl (meth) acrylate, 1,6-hexanediol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, trimethylolpropane di (meth) acrylate,
Trimethylolethane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, or (meth) acrylate represented by the following structural formula (2), and the like,
【0028】[0028]
【化2】 [Chemical 2]
【0029】〔式中、R2 は水素原子またはメチル基を
示し、mは1〜15、好ましくは1〜4の整数を示
す〕、さらにアルキルグリシジルエーテル、アリルグリ
シジルエーテル、グリシジル(メタ)アクリレート等の
グリシジル基含有化合物と(メタ)アクリル酸との付加
反応により得られる化合物も挙げることができる。これ
らのうち、特に2−ヒドロキシエチル(メタ)アクリレ
ート、2−ヒドロキシプロピル(メタ)アクリレート、
4−ヒドロキシブチル(メタ)アクリレート等が好まし
い。[Wherein, R 2 represents a hydrogen atom or a methyl group, m represents an integer of 1 to 15, preferably 1 to 4], and further alkyl glycidyl ether, allyl glycidyl ether, glycidyl (meth) acrylate, etc. The compound obtained by the addition reaction of the glycidyl group-containing compound and the (meth) acrylic acid can also be mentioned. Among these, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate,
4-hydroxybutyl (meth) acrylate and the like are preferable.
【0030】ウレタン(メタ)アクリレートの合成方法
は特に制限されないが、例えば次の(i)〜(iii)の
方法に従って行われる。
(i)(b)ポリイソシアネートおよび(c)水酸基含
有(メタ)アクリレートを反応させ、次いで(a)ポリ
オールの順に反応させる方法。
(ii)(a)ポリオール、(b)ポリイソシアネート、
(c)水酸基含有(メタ)アクリレートを一括に仕込ん
で反応させる方法。
(iii)(a)ポリオールおよび(b)ポリイソシアネ
ートを反応させ、次いで(c)水酸基含有(メタ)アク
リレートを反応させる方法。The method for synthesizing the urethane (meth) acrylate is not particularly limited, but it is carried out, for example, according to the following methods (i) to (iii). (I) A method in which (b) polyisocyanate and (c) hydroxyl group-containing (meth) acrylate are reacted, and then (a) polyol is reacted in that order. (Ii) (a) polyol, (b) polyisocyanate,
(C) A method in which hydroxyl group-containing (meth) acrylates are charged all at once and reacted. (Iii) A method of reacting (a) polyol and (b) polyisocyanate, and then reacting with (c) hydroxyl group-containing (meth) acrylate.
【0031】本発明で用いるウレタン(メタ)アクリレ
ートの合成においては通常、ナフテン酸銅、ナフテン酸
コバルト、ナフテン酸亜鉛、ジラウリル酸ジ−n−ブチ
ルスズ、トリエチルアミン、1,4−ジアザビシクロ
〔2.2.2〕オクタン、1,4−ジアザ−2−メチル
ビシクロ〔2.2.2〕オクタン等のウレタン化触媒
を、反応物の総量100重量部に対して0.01〜1重
量部用いて反応を行うのが好ましい。この反応における
反応温度は、通常0〜90℃、好ましくは10〜80℃
である。In the synthesis of the urethane (meth) acrylate used in the present invention, copper naphthenate, cobalt naphthenate, zinc naphthenate, di-n-butyltin dilaurate, triethylamine, 1,4-diazabicyclo [2.2. 2] Octane and 1,4-diaza-2-methylbicyclo [2.2.2] octane are used in an amount of 0.01 to 1 part by weight with respect to 100 parts by weight of the total amount of the reaction product as a urethane-forming catalyst. It is preferable to carry out. The reaction temperature in this reaction is usually 0 to 90 ° C, preferably 10 to 80 ° C.
Is.
【0032】本発明で用いるウレタン(メタ)アクリレ
ートの好ましい数平均分子量は、400〜20000で
あり、特に600〜10000であることが好ましい。The number average molecular weight of the urethane (meth) acrylate used in the present invention is preferably 400 to 20,000, particularly preferably 600 to 10,000.
【0033】本発明で用いる成分(A)のウレタン(メ
タ)アクリレートは、基材に対する密着力と組成物の粘
度の点から、組成物中に、成分(A)と成分(B)と成
分(C)の合計の重量を100重量部として、5〜70
重量部含まれるのが好ましい。The urethane (meth) acrylate of the component (A) used in the present invention has a component (A), a component (B) and a component (B) in the composition from the viewpoint of adhesion to a substrate and viscosity of the composition. 5 to 70 based on the total weight of C) as 100 parts by weight.
It is preferably included in parts by weight.
【0034】本発明で用いる(B)成分としては2−ヒ
ドロキシエチル(メタ)アクリレート、2−ヒドロキシ
プロピル(メタ)アクリレート、4−ヒドロキシブチル
(メタ)アクリレートのヒドロキシC1−C6 アルキル
(メタ)アクリレートを挙げることができる。(B)成
分は耐湿熱性を向上させるのに役立つが、中でも4−ヒ
ドロキシブチル(メタ)アクリレートが好ましい。As the component (B) used in the present invention, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and hydroxy C 1 -C 6 alkyl (meth) of 4-hydroxybutyl (meth) acrylate. Mention may be made of acrylates. The component (B) serves to improve resistance to moist heat, but 4-hydroxybutyl (meth) acrylate is preferred.
【0035】これらの市販品としては、HEA、HP
A、4HBA(以上、大阪有機化学工業(株)製)、ラ
イトエステルHOA、ライトエステルHOP−A、ライ
トエステルHO、ライトエステルHOP、ライトエステ
ルHOB(以上、共栄社化学(株)製)等が挙げられ
る。HEA and HP are commercially available products.
A, 4HBA (all manufactured by Osaka Organic Chemical Industry Co., Ltd.), light ester HOA, light ester HOP-A, light ester HO, light ester HOP, light ester HOB (all manufactured by Kyoeisha Chemical Co., Ltd.) and the like. To be
【0036】(B)成分であるヒドロキシアルキル(メ
タ)アクリレートは、耐湿熱性向上効果の点から、
(A)成分と(B)成分と(C)成分の重量を100重
量部として、本発明の組成物中に20〜90重量部配合
するのが好ましい。The component (B), a hydroxyalkyl (meth) acrylate, has the effect of improving wet heat resistance.
It is preferable that 20 to 90 parts by weight of the component (A), the component (B) and the component (C) are added to the composition of the present invention, with the weight being 100 parts by weight.
【0037】光重合開始剤である(C)成分は、2,2
−ジメトキシ−1,2−ジフェニルエタン−1−オン、
2−ヒドロキシ−2−メチル−1−フェニル−プロパン
−1−オンおよび/または1−ヒドロキシ−シクロヘキ
シルフェニルケトンであるが、このうち2,2−ジメト
キシ−1,2−ジフェニルエタン−1−オンおよび/ま
たは2−ヒドロキシ−2−メチル−1−フェニル、プロ
パン−1−オンが好ましい。(C)成分の含有量は、組
成物中、耐湿熱性および硬化性の点から、(A)成分と
(B)成分と(C)成分の重量を100重量部として、
好ましくは0.1〜20重量部、より好ましくは0.5
〜15重量部、特に好ましくは1〜10重量部である。The component (C) which is a photopolymerization initiator is 2,2
-Dimethoxy-1,2-diphenylethan-1-one,
2-hydroxy-2-methyl-1-phenyl-propan-1-one and / or 1-hydroxy-cyclohexyl phenyl ketone, of which 2,2-dimethoxy-1,2-diphenylethan-1-one and / Or 2-hydroxy-2-methyl-1-phenyl and propan-1-one are preferable. The content of the component (C) is 100 parts by weight based on the weight of the component (A), the component (B) and the component (C) from the viewpoint of resistance to moist heat and curability in the composition.
Preferably 0.1 to 20 parts by weight, more preferably 0.5.
-15 parts by weight, particularly preferably 1-10 parts by weight.
【0038】市販品としては、IRUGACURE18
4、同500、同651、DAROCUR1173、同
4265(以上チバガイギー社製)等が挙げられる。As a commercially available product, IRUGACURE18
4, 500, 651, DAROCUR1173, 4265 (all manufactured by Ciba Geigy) and the like.
【0039】本発明の組成物には、(A)成分、(B)
成分、(C)成分の他に(D)成分として一分子中に
(メタ)アクリロイル基を少なくとも一個有する(B)
成分以外の(メタ)アクリレート化合物を含有させるこ
とができる。(D)成分としては、(メタ)アクリロイ
ル基を一つだけ有する単官能化合物と二つ以上有する多
官能化合物の何れの化合物を用いてもよく、適当な比率
で併用してもよい。The composition of the present invention comprises (A) component, (B)
In addition to the component and the component (C), at least one (meth) acryloyl group is contained in one molecule as the component (D) (B)
A (meth) acrylate compound other than the components can be contained. As the component (D), any one of a monofunctional compound having only one (meth) acryloyl group and a polyfunctional compound having two or more (meth) acryloyl groups may be used, and they may be used in combination at an appropriate ratio.
【0040】上記単官能化合物としては、例えばメチル
(メタ)アクリレート、エチル(メタ)アクリレート、
プロピル(メタ)アクリレート、イソプロピル(メタ)
アクリレート、ブチル(メタ)アクリレート、アミル
(メタ)アクリレート、イソブチル(メタ)アクリレー
ト、t−ブチル(メタ)アクリレート、ペンチル(メ
タ)アクリレート、イソアミル(メタ)アクリレート、
ヘキシル(メタ)アクリレート、ヘプチル(メタ)アク
リレート、オクチル(メタ)アクリレート、イソオクチ
ル(メタ)アクリレート、2−エチルヘキシル(メタ)
アクリレート、ノニル(メタ)アクリレート、デシル
(メタ)アクリレート、イソデシル(メタ)アクリレー
ト、ウンデシル(メタ)アクリレート、ドデシル(メ
タ)アクリレート、ラウリル(メタ)アクリレート、オ
クタデシル(メタ)アクリレート、ステアリル(メタ)
アクリレート、テトラヒドロフルフリル(メタ)アクリ
レート、ブトキシエチル(メタ)アクリレート、エトキ
シジエチレングリコール(メタ)アクリレート、ベンジ
ル(メタ)アクリレート、シクロヘキシル(メタ)アク
リレート、フェノキシエチル(メタ)アクリレート、ポ
リエチレングリコールモノ(メタ)アクリレート、ポリ
プロピレングリコールモノ(メタ)アクリレート、メト
キシエチレングリコールモノ(メタ)アクリレート、エ
トキシエチル(メタ)アクリレート、エトキシエトキシ
エチル(メタ)アクリレート、メトキシポリエチレング
リコール(メタ)アクリレート、メトキシポリプロピレ
ングリコール(メタ)アクリレート、ジシクロペンタジ
エニル(メタ)アクリレート、ジシクロペンタニル(メ
タ)アクリレート、ジシクロペンテニル(メタ)アクリ
レート、トリシクロデカニル(メタ)アクリレート、ボ
ルニル(メタ)アクリレート、イソボルニル(メタ)ア
クリレート、アダマンチル(メタ)アクリレート、ジメ
チルアミノエチル(メタ)アクリレート、ジエチルアミ
ノエチル(メタ)アクリレート、7−アミノ−3,7−
ジメチルオクチル(メタ)アクリレート、(メタ)アク
リロイルモルホリン、2−(メタ)アクリロイルオキシ
エチルフタル酸、2−(メタ)アクリロイルオキシエチ
ルヘキサヒドロフタル酸、2−(メタ)アクリロイルオ
キシプロピルフタル酸、2−(メタ)アクリロイルオキ
シプロピルテトラヒドロフタル酸、2−(メタ)アクリ
ロイルオキシプロピルヘキサヒドロフタル酸、2−(メ
タ)アクリロイルオキシエチルコハク酸、トリフルオロ
エチル(メタ)アクリレート、テトラフルオロプロピル
(メタ)アクリレート、ヘキサフルオロプロピル(メ
タ)アクリレート、オクタフルオロペンチル(メタ)ア
クリレート、ヘプタデカフルオロデシル(メタ)アクリ
レート、モノ〔2−(メタ)アクリロイルオキシエチ
ル〕ホスフェート、モノ〔2−(メタ)アクリロイルオ
キシエチル〕ジフェニルホスフェート、モノ〔2−(メ
タ)アクリロイルオキシプロピル〕ホスフェート、下記
式(3)〜(5)で表される化合物を挙げることができ
る。Examples of the monofunctional compound include methyl (meth) acrylate, ethyl (meth) acrylate,
Propyl (meth) acrylate, isopropyl (meth)
Acrylate, butyl (meth) acrylate, amyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, isoamyl (meth) acrylate,
Hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth)
Acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, octadecyl (meth) acrylate, stearyl (meth)
Acrylate, tetrahydrofurfuryl (meth) acrylate, butoxyethyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenoxyethyl (meth) acrylate, polyethylene glycol mono (meth) acrylate , Polypropylene glycol mono (meth) acrylate, methoxyethylene glycol mono (meth) acrylate, ethoxyethyl (meth) acrylate, ethoxyethoxyethyl (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, di Cyclopentadienyl (meth) acrylate, dicyclopentanyl (meth) acrylate Dicyclopentenyl (meth) acrylate, tricyclodecanyl (meth) acrylate, bornyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 7-amino-3,7-
Dimethyloctyl (meth) acrylate, (meth) acryloylmorpholine, 2- (meth) acryloyloxyethylphthalic acid, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxypropylphthalic acid, 2- (Meth) acryloyloxypropyltetrahydrophthalic acid, 2- (meth) acryloyloxypropylhexahydrophthalic acid, 2- (meth) acryloyloxyethylsuccinic acid, trifluoroethyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, Hexafluoropropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, mono [2- (meth) acryloyloxyethyl] phosphate, molybdenum [2- (meth) acryloyloxyethyl] diphenyl phosphate, mono [2- (meth) acryloyloxy propyl] phosphate, the following formula (3) include a compound represented by - (5).
【0041】[0041]
【化3】 [Chemical 3]
【0042】〔式中、R3 は炭素数2〜6のアルキレン
基またはヒドロキシアルキレン基を示し、R4 は水素原
子またはメチル基を示し、R5 は水素原子または炭素数
1〜12のアルキル基を示し、pは0〜20の整数を示
す。〕[In the formula, R 3 represents an alkylene group or a hydroxyalkylene group having 2 to 6 carbon atoms, R 4 represents a hydrogen atom or a methyl group, and R 5 represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. Is shown and p shows the integer of 0-20. ]
【0043】[0043]
【化4】 [Chemical 4]
【0044】〔式中、R6 は水素原子またはメチル基を
示し、R7 は炭素数2〜8のアルキレン基を示し、qは
0〜8の整数を示す。〕[In the formula, R 6 represents a hydrogen atom or a methyl group, R 7 represents an alkylene group having 2 to 8 carbon atoms, and q represents an integer of 0 to 8. ]
【0045】[0045]
【化5】 [Chemical 5]
【0046】〔式中、R8 は水素原子またはメチル基を
示し、R9 は炭素数2〜8のアルキレン基を示し、rは
0〜8の整数を示し、R10およびR11は水素原子、炭素
数1〜6のアルキル基を示す。〕[In the formula, R 8 represents a hydrogen atom or a methyl group, R 9 represents an alkylene group having 2 to 8 carbon atoms, r represents an integer of 0 to 8, and R 10 and R 11 represent a hydrogen atom. Represents an alkyl group having 1 to 6 carbon atoms. ]
【0047】これらの市販品としては、アロニックス
M101、M102、M110、M111、M113、
M114、M117、M120、M152、M154、
M5300、M5400、M5500、M5600(以
上、東亞合成(株)製)、KAYARAD TC−11
0S、R−128H、R629、R644(以上、日本
化薬(株)製)、IPAA、AIB、SBAA、TB
A、IAAA、HEXA、CHA、NOAA、IOA
A、INAA、LA、TDA、MSAA、CAA、HD
AA、LTA、STA、ISAA−1、ODAA、ND
AA、IBXA、ADAA、TCDA、2−MTA、D
MA、ビスコート #150、#150D、#155、
#158、#160、#190、#190D、#19
2、#193、#220、#320、#2311HP、
#2000、#2100、#2150、#2180、M
TG(以上、大阪有機化学工業(株)製)、NKエステ
ル M−20G、M−40G、M−90G、M−230
G、CB−1、SA、S、AMP−10G、AMP−2
0G、AMP−60G、AMP−90G、A−SA、N
LA(以上、新中村化学工業(株)製)、ACMO
((株)興人製)、ライトアクリレート IA−A、L
−A、S−A、BO−A、EC−A、MTG−A、DP
M−A、PO−A、P−200A、THF−A、IB−
XA、HOA−MS、HOA−MPL、HOA−MP
E、HOA−HH、IO−A、BZ−A、NP−EA、
NP−10EA、HOB−A、FA−108、エポキシ
エステルM−600A、ライトエステルP−M(以上、
共栄社化学(株)製)、FA−511、FA−512
A、FA−513A(以上、日立化成工業(株)製)、
AR−100、MR−100、MR−200、MR−2
60(以上、大八化学(株)製)、JAMP−100、
JAMP−514、JPA−514(以上、城北化学
(株)製)等が挙げられる。These commercially available products include Aronix
M101, M102, M110, M111, M113,
M114, M117, M120, M152, M154,
M5300, M5400, M5500, M5600 (above, manufactured by Toagosei Co., Ltd.), KAYARAD TC-11
0S, R-128H, R629, R644 (Nippon Kayaku Co., Ltd.), IPAA, AIB, SBAA, TB
A, IAAA, HEXA, CHA, NOAA, IOA
A, INAA, LA, TDA, MSAA, CAA, HD
AA, LTA, STA, ISAA-1, ODAA, ND
AA, IBXA, ADAA, TCDA, 2-MTA, D
MA, viscoat # 150, # 150D, # 155,
# 158, # 160, # 190, # 190D, # 19
2, # 193, # 220, # 320, # 2311HP,
# 2000, # 2100, # 2150, # 2180, M
TG (above, manufactured by Osaka Organic Chemical Industry Co., Ltd.), NK ester M-20G, M-40G, M-90G, M-230
G, CB-1, SA, S, AMP-10G, AMP-2
0G, AMP-60G, AMP-90G, A-SA, N
LA (above, Shin-Nakamura Chemical Co., Ltd.), ACMO
(Manufactured by Kojin Co., Ltd.), light acrylate IA-A, L
-A, S-A, BO-A, EC-A, MTG-A, DP
M-A, PO-A, P-200A, THF-A, IB-
XA, HOA-MS, HOA-MPL, HOA-MP
E, HOA-HH, IO-A, BZ-A, NP-EA,
NP-10EA, HOB-A, FA-108, epoxy ester M-600A, light ester PM (above,
Kyoeisha Chemical Co., Ltd.), FA-511, FA-512
A, FA-513A (above, manufactured by Hitachi Chemical Co., Ltd.),
AR-100, MR-100, MR-200, MR-2
60 (above, manufactured by Daihachi Chemical Co., Ltd.), JAMP-100,
Examples thereof include JAMP-514 and JPA-514 (above, manufactured by Johoku Chemical Co., Ltd.).
【0048】また、上記多官能化合物としては、例えば
エチレングリコールジ(メタ)アクリレート、プロピレ
ングリコールジ(メタ)アクリレート、1,4−ブタン
ジオールジ(メタ)アクリレート、1,6−ヘキサンジ
オールジ(メタ)アクリレート、1,9−ノナンジオー
ルジ(メタ)アクリレート、ジエチレングリコールジ
(メタ)アクリレート、トリエチレングリコールジ(メ
タ)アクリレート、テトラエチレングリコールジ(メ
タ)アクリレート、ポリエチレングリコールジ(メタ)
アクリレート、ジプロピレングリコールジ(メタ)アク
リレート、トリプロピレングリコールジ(メタ)アクリ
レート、ポリプロピレングリコールジ(メタ)アクリレ
ート、ネオペンチルグリコールジ(メタ)アクリレー
ト、ヒドロキシピバリン酸ネオペンチルグリコールジ
(メタ)アクリレート、トリメチロールプロパントリ
(メタ)アクリレート、ペンタエリスリトールトリ(メ
タ)アクリレート、ペンタエリスリトールテトラ(メ
タ)アクリレート、ジトリメチロールプロパンテトラ
(メタ)アクリレート、ジペンタエリスリトールペンタ
(メタ)アクリレート、ジペンタエリスリトールヘキサ
(メタ)アクリレート、トリメチロールプロパントリオ
キシエチル(メタ)アクリレート、トリメチロールプロ
パンポリオキシエチル(メタ)アクリレート、トリメチ
ロールプロパントリオキシプロピル(メタ)アクリレー
ト、トリメチロールプロパンポリオキシエチル(メタ)
アクリレート、トリス(2−ヒドロキシエチル)イソシ
アヌレートジ(メタ)アクリレート、トリス(2−ヒド
ロキシエチル)イソシアヌレートトリ(メタ)アクリレ
ート、エチレンオキシド付加ビスフェノールAジ(メ
タ)アクリレート、エチレンオキシド付加ビスフェノー
ルFジ(メタ)アクリレート、プロピレンオキシド付加
ビスフェノールAジ(メタ)アクリレート、プロピレン
オキシド付加ビスフェノールFジ(メタ)アクリレー
ト、トリシクロデカンジメタノールジ(メタ)アクリレ
ート、ビスフェノールAジエポキシジ(メタ)アクリレ
ート、ビスフェノールFジエポキシジ(メタ)アクリレ
ート、ビス〔2−(メタ)アクリロイルオキシエチル〕
ホスフェート、ビス〔2−(メタ)アクリロイルオキシ
プロピル〕ホスフェート、トリス〔2−(メタ)アクリ
ロイルオキシエチル〕ホスフェート等が挙げられる。Examples of the polyfunctional compound include ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth). ) Acrylate, 1,9-nonanediol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth)
Acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, hydroxypivalic acid neopentyl glycol di (meth) acrylate, tri Methylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate , Trimethylolpropane trioxyethyl (meth) acrylate, trimethylolpropane polyoxyethyl (meth Acrylate, trimethylolpropane tri propyl (meth) acrylate, trimethylolpropane polyoxyethylene (meth)
Acrylate, tris (2-hydroxyethyl) isocyanurate di (meth) acrylate, tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate, ethylene oxide-added bisphenol A di (meth) acrylate, ethylene oxide-added bisphenol F di (meth) acrylate Acrylate, propylene oxide-added bisphenol A di (meth) acrylate, propylene oxide-added bisphenol F di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, bisphenol A diepoxy di (meth) acrylate, bisphenol F diepoxy di (meth) acrylate , Bis [2- (meth) acryloyloxyethyl]
Phosphate, bis [2- (meth) acryloyloxypropyl] phosphate, tris [2- (meth) acryloyloxyethyl] phosphate and the like can be mentioned.
【0049】これらの市販品としては、SA−100
2、SA−2006、SA−2007、SA−410
0、 SA−5001、SA−6000、SA−760
0、SA−8000、SA−9000(以上、三菱化学
(株)製)、ビスコート #195、#195D、#2
14HP、#215、#215D、#230、#230
D、#260、#295、#295D、#300、#3
10HP、#310HG、#312、#335HP、#
335D、#360、GPT、#400、V#540、
#700、GPT(以上、大阪有機化学工業(株)
製)、KAYARADMANDA、R−526、NPG
DA、PEG400DA、R−167、HX−220、
HX−620、R−551、R−712、R−604、
R−684、GPO−303、TMPTA、THE−3
30、TPA−320、TPA−330、PET−3
0、RP−1040、T−1420、DPHA、D−3
10、D−330、DPCA−20、DPCA−30、
DPCA−60、DPCA−120(以上、日本化薬
(株)製)、アロニックス M−210、M−208、
M−215、M−220、M−225、M−233、M
−240、M−245、M−260、M−270、M−
305、M−309、M−310、M−315、M−3
20、M−350、M−360、M−400、M−40
8、M−450(以上、東亞合成(株)製)、SR−2
12、SR−213、SR−355(以上、サートマー
社製)、SP−1506、SP−1507、SP−15
09、SP−1519−1、SP−1563、SP−2
500、VR60、VR77、VR90(以上、昭和高
分子(株)製)、ライトエステルP−2M(以上、共栄
社化学(株)製)、ビスコート3PA(大阪有機化学工
業(株)製)、EB−169、EB−179、EB−3
603、R−DX63182(以上、ダイセルUCB
(株)製)等が挙げられる。(D)成分は、組成物を粘
度、Tg、屈折率等を所望の範囲とするために使用され
る。(D)成分の使用量は、(B)成分の70%以内を
置き換える形で使用するのが好ましい。These commercially available products include SA-100.
2, SA-2006, SA-2007, SA-410
0, SA-5001, SA-6000, SA-760
0, SA-8000, SA-9000 (above, manufactured by Mitsubishi Chemical Corporation), Viscoat # 195, # 195D, # 2.
14 HP, # 215, # 215D, # 230, # 230
D, # 260, # 295, # 295D, # 300, # 3
10 HP, # 310HG, # 312, # 335HP, #
335D, # 360, GPT, # 400, V # 540,
# 700, GPT (above, Osaka Organic Chemical Industry Co., Ltd.)
), KAYARDAMANDA, R-526, NPG
DA, PEG400DA, R-167, HX-220,
HX-620, R-551, R-712, R-604,
R-684, GPO-303, TMPTA, THE-3
30, TPA-320, TPA-330, PET-3
0, RP-1040, T-1420, DPHA, D-3
10, D-330, DPCA-20, DPCA-30,
DPCA-60, DPCA-120 (above, Nippon Kayaku Co., Ltd. product), Aronix M-210, M-208,
M-215, M-220, M-225, M-233, M
-240, M-245, M-260, M-270, M-
305, M-309, M-310, M-315, M-3
20, M-350, M-360, M-400, M-40
8, M-450 (all manufactured by Toagosei Co., Ltd.), SR-2
12, SR-213, SR-355 (above, manufactured by Sartomer), SP-1506, SP-1507, SP-15.
09, SP-1519-1, SP-1563, SP-2
500, VR60, VR77, VR90 (above, Showa High Polymer Co., Ltd.), light ester P-2M (above, Kyoeisha Chemical Co., Ltd.), Viscoat 3PA (Osaka Organic Chemical Industry Co., Ltd.), EB- 169, EB-179, EB-3
603, R-DX63182 (above, Daicel UCB
(Manufactured by Co., Ltd.) and the like. The component (D) is used to adjust the viscosity, Tg, refractive index, etc. of the composition to a desired range. The amount of the component (D) used is preferably such that 70% or less of the component (B) is replaced.
【0050】本発明の組成物には、(A)成分、(B)
成分、(C)成分の他に(E)成分として(C)成分以
外の光重合開始剤を含めることができる。(E)成分の
光重合開始剤としては、例えば、3−メチルアセトフェ
ノン、2,2−ジメトキシ−2−フェニルアセトフェノ
ン、キサントン、フルオレノン、ベンズアルデヒド、フ
ルオレン、アントラキノン、トリフェニルアミン、カル
バゾール、3−メチルアセトフェノン、ベンゾフェノ
ン、4−クロロベンゾフェノン、4,4′−ジメトキシ
ベンゾフェノン、4,4′−ジアミノベンゾフェノン、
ベンゾインエチルエーテル、ベンゾインプロピルエーテ
ル、ミヒラーズケトン、ベンジルジメチルケタール、1
−(4−イソプロピルフェニル)−2−ヒドロキシ−2
−メチルプロパン−1−オン、1−(4−ドデシルフェ
ニル)−2−ヒドロキシ−2−メチルプロパン−1−オ
ン、4−(2−ヒドロキシエトキシ)フェニル−(2−
ヒドロキシ−2−プロピル)ケトン、2−メチル−1−
[4−(メチルチオ)フェニル]−2−モルホリノ−プ
ロパン−1−オン、2,4,6−トリメチルベンゾイル
フェニルフォスフィネート、2,4,6−トリメチルベ
ンゾイルジフェニルフォスフィンオキシド、2−ベンジ
ル−2−ジメチルアミノ−1−(4−モルホリノフェニ
ル)−ブタン−1−オン、ビス(2,6−ジメトキシベ
ンゾイル)−2,4,4−トリメチルペンチルホスフィ
ンオキシド、メチルベンゾイルホルメート、チオキサン
トン、ジエチルチオキサントン、2−イソプロピルチオ
キサントン、2−クロロチオキサントン、オリゴ[2−
ヒドロキシ−2−メチル−1−[4−(1−メチルビニ
ル)フェニル]プロパノン]等が挙げられる。The composition of the present invention includes the component (A) and the component (B).
In addition to the component and the component (C), a photopolymerization initiator other than the component (C) can be included as the component (E). Examples of the photopolymerization initiator as the component (E) include 3-methylacetophenone, 2,2-dimethoxy-2-phenylacetophenone, xanthone, fluorenone, benzaldehyde, fluorene, anthraquinone, triphenylamine, carbazole, and 3-methylacetophenone. , Benzophenone, 4-chlorobenzophenone, 4,4'-dimethoxybenzophenone, 4,4'-diaminobenzophenone,
Benzoin ethyl ether, benzoin propyl ether, Michler's ketone, benzyl dimethyl ketal, 1
-(4-Isopropylphenyl) -2-hydroxy-2
-Methylpropan-1-one, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-
Hydroxy-2-propyl) ketone, 2-methyl-1-
[4- (Methylthio) phenyl] -2-morpholino-propan-1-one, 2,4,6-trimethylbenzoylphenylphosphinate, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2-benzyl-2 -Dimethylamino-1- (4-morpholinophenyl) -butan-1-one, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, methylbenzoyl formate, thioxanthone, diethylthioxanthone, 2-isopropylthioxanthone, 2-chlorothioxanthone, oligo [2-
Hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propanone] and the like.
【0051】これらの市販品としては、IRUGACU
RE261、369、907、CGI−403、81
9、1700、1800、1850(以上、チバスペシ
ャルティケミカルス(株)製)、Lucirin TP
O、LR8728、LR8893(以上、BASF社
製)、Darocur 953、1116、1664、
2273、2959、ZL1 3331(以上、メルク
社製)、ユベクリルP36(UCB社製)、VICUR
E55(アクゾ社製)、ESACURE KIP100
F、KIP150(LAMBERTI社製)、KAYA
KUREI TX、QTX、DETX、BMS(以上、
日本化薬(株)製)等を挙げることができる。(E)成
分は、組成物の表面硬化性、硬化速度を高めるために使
用される。(E)成分の使用量は、(C)成分の70%
以内を置き換える形で使用するのが好ましい。These commercially available products include IRUGACU.
RE261, 369, 907, CGI-403, 81
9, 1700, 1800, 1850 (above, manufactured by Ciba Specialty Chemicals Co., Ltd.), Lucirin TP
O, LR8728, LR8893 (above, manufactured by BASF), Darocur 953, 1116, 1664,
2273, 2959, ZL1 3331 (above, manufactured by Merck), Yubecryl P36 (manufactured by UCB), VICUR
E55 (manufactured by Akzo), ESACURE KIP100
F, KIP150 (manufactured by LAMBERTI), KAYA
KUREI TX, QTX, DETX, BMS (above,
Nippon Kayaku Co., Ltd. etc. can be mentioned. The component (E) is used for increasing the surface curability and the curing speed of the composition. The amount of component (E) used is 70% of that of component (C).
It is preferable to use it in the form of replacing the inside.
【0052】本発明の組成物には、(A)成分、(B)
成分、(C)成分の他に(F)成分として、アクリル基
を含む化合物以外のラジカル重合性化合物を含むことが
できる。このような化合物としては、N−ビニルピロリ
ドン、N−ビニルカプロラクタム、酢酸ビニル、プロピ
オン酸ビニル、スチレン、ジビニルベンゼン、不飽和ポ
リエステル等を挙げることができる。上記不飽和ポリエ
ステルはラジカル重合性不飽和二重結合を有するジカル
ボン酸とアルコール類のエステルであり、ラジカル重合
性不飽和二重結合を有するジカルボン酸としては無水マ
レイン酸、イタコン酸、フマル酸を挙げることができ、
アルコール類としては、メタノール、エタノール、n−
プロピルアルコール、iso−プロピルアルコール、n
−ブチルアルコール、iso−ブチルアルコール、se
c−ブチルアルコール、tert−ブチルアルコール、
n−ヘキサノール、シクロヘキサノール、2−エチルヘ
キシルアルコール等の一価アルコール;エチレングリコ
ール、ジエチレングリコール、トリエチレングリコール
等の(ポリ)エチレングリコール類;プロピレングリコ
ール、ジプロピレングリコール、トリプロピレングリコ
ール等の(ポリ)プロピレングリコール類;1,6−ヘ
キサンジオール等の二 価アルコール;グリセリン、ト
リメチロールプロパン等の三価アルコール等が挙げられ
る。The composition of the present invention includes the component (A) and the component (B).
In addition to the component and the component (C), the component (F) may contain a radically polymerizable compound other than the compound containing an acrylic group. Examples of such compounds include N-vinylpyrrolidone, N-vinylcaprolactam, vinyl acetate, vinyl propionate, styrene, divinylbenzene and unsaturated polyester. The unsaturated polyester is an ester of a dicarboxylic acid having a radical-polymerizable unsaturated double bond and an alcohol, and examples of the dicarboxylic acid having a radical-polymerizable unsaturated double bond include maleic anhydride, itaconic acid, and fumaric acid. It is possible,
As alcohols, methanol, ethanol, n-
Propyl alcohol, iso-propyl alcohol, n
-Butyl alcohol, iso-butyl alcohol, se
c-butyl alcohol, tert-butyl alcohol,
Monohydric alcohols such as n-hexanol, cyclohexanol and 2-ethylhexyl alcohol; (poly) ethylene glycols such as ethylene glycol, diethylene glycol and triethylene glycol; (poly) propylene such as propylene glycol, dipropylene glycol and tripropylene glycol. Glycols; dihydric alcohols such as 1,6-hexanediol; trihydric alcohols such as glycerin and trimethylolpropane.
【0053】また、本発明の組成物には、その他の添加
剤として、エポキシ樹脂、ポリアミド、ポリアミドイミ
ド、ポリウレタン、ポリブタジエン、クロロプレン、ポ
リエーテル、ポリエステル、ペンタジエン誘導体、SB
S(スチレン/ブタジエン/スチレンブロック共重合
体)、SBSの水添物、SIS(スチレン/イソプレン
/スチレンブロック共重合体)、石油樹脂、キシレン樹
脂、ケトン樹脂、フッ素系オリゴマー、シリコーン系オ
リゴマー、ポリスルフィド系オリゴマー等を配合するこ
とができる。In the composition of the present invention, other additives such as epoxy resin, polyamide, polyamideimide, polyurethane, polybutadiene, chloroprene, polyether, polyester, pentadiene derivative, SB
S (styrene / butadiene / styrene block copolymer), SBS hydrogenated product, SIS (styrene / isoprene / styrene block copolymer), petroleum resin, xylene resin, ketone resin, fluorine-based oligomer, silicone-based oligomer, polysulfide A system oligomer etc. can be blended.
【0054】さらに上記以外の各種塗料添加剤、例えば
酸化防止剤、紫外線吸収剤、光安定剤、老化防止剤、シ
ランカップリング剤、消泡剤、レベリング剤、帯電防止
剤、界面活性剤、保存安定剤、熱重合禁止剤、可塑剤、
濡れ性改良剤等を必要に応じて配合することもできる。
例えば、酸化防止剤としては、Irganox 24
5、259、565、1010、1035、1076、
1081、1098、1222、1330(以上、チバ
スペシャルティケミカルズ(株)製)等が挙げられる。Further, various coating additives other than the above, for example, antioxidants, ultraviolet absorbers, light stabilizers, antiaging agents, silane coupling agents, defoamers, leveling agents, antistatic agents, surfactants, preservatives Stabilizer, thermal polymerization inhibitor, plasticizer,
A wettability improver and the like can be added if necessary.
For example, as an antioxidant, Irganox 24
5, 259, 565, 1010, 1035, 1076,
1081, 1098, 1222, 1330 (all manufactured by Ciba Specialty Chemicals Co., Ltd.) and the like.
【0055】紫外線吸収剤としてはベンゾトリアゾール
系、トリアジン系の紫外線吸収剤が挙げられ、市販品と
しては、Tinuvin P、234、320、32
6、327、328、213、400(以上、チバスペ
シャルティケミカルズ(株)製)、Sumisorb
110、130、140、220、250、300、3
20、340、350、400(以上、住友化学(株)
製)等が挙げられる。Examples of the ultraviolet absorber include benzotriazole type and triazine type ultraviolet absorbers, and commercially available products are Tinuvin P, 234, 320, 32.
6,327,328,213,400 (above, manufactured by Ciba Specialty Chemicals Co., Ltd.), Sumisorb
110, 130, 140, 220, 250, 300, 3
20, 340, 350, 400 (above, Sumitomo Chemical Co., Ltd.)
Manufactured) and the like.
【0056】光安定剤としては、Tinuvin 14
4、292、622LD(以上、チバスペシャルティケ
ミカルズ(株)製)サノールLS440、LS770
(以上、三共(株)製)、Sumisorb TM−0
61(住友化学(株)製)等が挙げられ、本発明の組成
物全体を100重量部とした時、5重量部以下配合する
のが好ましい。As the light stabilizer, Tinuvin 14
4,292,622LD (above, Ciba Specialty Chemicals Co., Ltd.) SANOL LS440, LS770
(Above, Sankyo Co., Ltd. product), Sumisorb TM-0
61 (manufactured by Sumitomo Chemical Co., Ltd.) and the like, and when the total amount of the composition of the present invention is 100 parts by weight, it is preferable to add 5 parts by weight or less.
【0057】老化防止剤としてはフェノール系老化防止
剤、アリルアミン系老化防止剤、ケトンアミン系系老化
防止剤等が挙げられ、それらの市販品としてはAnti
gen W、S、P、3C 、6C、RD−G、FR、
AW(以上、住友化学(株)製)等が挙げられる。シラ
ンカップリング剤としては、γ−メルカプトプロピルメ
チルモノメトキシシラン、γ−メルカプトプロピルメチ
ルジメトキシシラン、γ−メルカプトプロピルトリメト
キシシラン、γ−メルカプトプロピルモノエトキシシラ
ン、γ−メルカプトプロピルジエトキシシラン、γ−メ
ルカプトプロピルトリエトキシシラン、β−メルカプト
エチルモノエトキシシラン、β−メルカプトエチルトリ
エトキシシラン、β−メルカプトエチルトリエトキシシ
ラン、N−(2−アミノエチル)−3−アミノプロピル
メチルジメトキシシラン、N−(2−アミノエチル)−
3−アミノプロピルトリメトキシシラン、γ−アミノプ
ロピルトリエトキシシラン、γ−グリシドキシルプロピ
ルトリメトキシシラン、γ−グリシドキシルプロピルメ
チルジメトキシシラン、2−(3,4−エポキシシクロ
ヘキシル)エチルトリメトキシシラン、γ−クロロプロ
ピルメチルジメトキシシラン、γ−クロロプロピルトリ
メトキシシラン、γ−メタアクリロイルオキシプロピル
トリメトキシシラン等が挙げられる。これらの市販品と
しては、サイラエースS310、S311、S320、
S321、S330、S510、S520、S530、
S610、S620、S710、S810(以上、チッ
ソ(株)製)、SH6062、AY43−062、SH
6020、SZ6023、SZ6030、SH604
0、SH6076、SZ6083(以上、東レ・ダウコ
ーニング・シリコーン(株)製)、KBM403、KB
M503、KBM602、KBM603、KBM80
3、KBE903(以上、信越シリコーン(株)製)等
が挙げられる。Examples of the antiaging agent include a phenol antiaging agent, an allylamine antiaging agent, a ketone amine antiaging agent, and the like, and commercially available products thereof include Anti.
gen W, S, P, 3C, 6C, RD-G, FR,
AW (above, Sumitomo Chemical Co., Ltd. product) etc. are mentioned. As the silane coupling agent, γ-mercaptopropylmethylmonomethoxysilane, γ-mercaptopropylmethyldimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-mercaptopropylmonoethoxysilane, γ-mercaptopropyldiethoxysilane, γ- Mercaptopropyltriethoxysilane, β-mercaptoethylmonoethoxysilane, β-mercaptoethyltriethoxysilane, β-mercaptoethyltriethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- ( 2-aminoethyl)-
3-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-glycidoxylpropyltrimethoxysilane, γ-glycidoxylpropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ -Chloropropylmethyldimethoxysilane, γ-chloropropyltrimethoxysilane, γ-methacryloyloxypropyltrimethoxysilane and the like can be mentioned. These commercial products include Sila Ace S310, S311, S320,
S321, S330, S510, S520, S530,
S610, S620, S710, S810 (above, manufactured by Chisso Corporation), SH6062, AY43-062, SH
6020, SZ6023, SZ6030, SH604
0, SH6076, SZ6083 (above, Toray Dow Corning Silicone Co., Ltd.), KBM403, KB
M503, KBM602, KBM603, KBM80
3, KBE903 (above, manufactured by Shin-Etsu Silicone Co., Ltd.) and the like.
【0058】消泡剤としては、フローレンAC−20
2、AC−300、AC−303、AC−326F、A
C−900、AC−1190、AC−2000(以上、
共栄社油脂(株)製)を例とするSi原子やF原子を含
まない有機共重合体、フローレンAC−901、AC−
950、AC−1140、AO−3、AO−4OH(以
上、共栄社油脂(株)製)、FS1265、SH20
0、SH5500、SC5540、SC5570、F−
1、SD5590(以上、東レ・ダウコーニング・シリ
コーン(株)製)等のシリコン系消泡剤、メガファック
F−142D、F−144D、F−178K、F−17
9、F−815(以上、大日本インキ化学工業(株)
製)等のフッ素原子含有消泡剤等が挙げられる。As the defoaming agent, Floren AC-20
2, AC-300, AC-303, AC-326F, A
C-900, AC-1190, AC-2000 (above,
Organic copolymers containing no Si atom or F atom, such as Kyoeisha Yushi Co., Ltd., Floren AC-901, AC-
950, AC-1140, AO-3, AO-4OH (all manufactured by Kyoeisha Oil & Fat Co., Ltd.), FS1265, SH20.
0, SH5500, SC5540, SC5570, F-
1, SD5590 (above, manufactured by Toray Dow Corning Silicone Co., Ltd.), a silicon-based defoaming agent, Megafac F-142D, F-144D, F-178K, F-17.
9, F-815 (above, Dainippon Ink and Chemicals, Inc.)
And a fluorine atom-containing defoaming agent.
【0059】レベリング剤としては、ポリフローNo.
7、No.38、No.50E、S、75、No.7
5、No.77、No.90、No.95、No.30
0、No.460、ATF、KL−245(以上、共栄
社油脂(株)製)等が挙げられる。これらの添加剤の使
用量は、本発明の組成物の目的を阻害しない範囲で必要
に応じて決めることができる。As the leveling agent, Polyflow No.
7, No. 38, No. 50E, S, 75, No. 7
5, No. 77, No. 90, No. 95, No. Thirty
0, No. 460, ATF, KL-245 (above, Kyoeisha Yushi Co., Ltd. product) etc. are mentioned. The amount of these additives to be used can be determined as necessary within a range that does not impair the purpose of the composition of the present invention.
【0060】本発明の組成物の粘度は、好ましくは10
〜10000mPa・s、さらに好ましくは50〜50
00mPa・s、特に好ましくは150〜2000mP
a・sである。The viscosity of the composition of the present invention is preferably 10
To 10,000 mPa · s, more preferably 50 to 50
00 mPa · s, particularly preferably 150 to 2000 mP
a · s.
【0061】また、得られる硬化物のガラス転移温度が
通常、−30〜200℃、好ましくは0〜120℃にな
るように各成分を配合することが好ましい。ガラス転移
温度が低すぎると夏場や日当たりの良い閉め切った室内
等で高温になった場合硬化物が軟化して接着力が低下し
て被着体が剥がれたりずれたりする場合がある。逆に硬
化物がガラス転移温度が高すぎると十分な接着力が得ら
れなかったり、接着したものを落下したり曲げたりする
と割れる場合がある。Further, it is preferable to mix the respective components so that the glass transition temperature of the obtained cured product is usually -30 to 200 ° C, preferably 0 to 120 ° C. If the glass transition temperature is too low, the cured product may be softened and the adhesive strength may be lowered and the adherend may be peeled off or displaced when the temperature becomes high in the summer or in a sunny closed room. On the other hand, if the cured product has a glass transition temperature that is too high, a sufficient adhesive force may not be obtained, or the adhered product may crack when dropped or bent.
【0062】なお、ここでいうガラス転移温度は動的粘
弾性測定装置により振動周波数10で測定した 損失正
接(tanδ)の極大値を示す温度で定義される。The glass transition temperature mentioned here is defined as the temperature at which the loss tangent (tan δ) has a maximum value measured at a vibration frequency of 10 by a dynamic viscoelasticity measuring device.
【0063】本発明の組成物は、通常の光硬化型樹脂組
成物の場合と同様に紫外線、可視光線、電子線などの照
射により硬化させることができる。例えば、本発明の組
成物を接着剤層の厚みが10〜100μmになるよう被
着体間に満たし、メタルハライドランプで50〜200
0mJ/cm2 照射することで容易に硬化し被着体どう
しを接着することができる。The composition of the present invention can be cured by irradiation with ultraviolet rays, visible rays, electron beams or the like, as in the case of a usual photocurable resin composition. For example, the composition of the present invention is filled between the adherends so that the adhesive layer has a thickness of 10 to 100 μm, and a metal halide lamp is used for 50 to 200 μm.
By irradiating with 0 mJ / cm 2, it is possible to easily cure and adhere the adherends to each other.
【0064】また、本発明の組成物の光硬化物は透明性
に優れることが望ましく、例えば厚さ60μmの硬化物
の600〜700nmでの光透過率が、通常90%以上
になることが望ましい。光透過率が90%未満であると
光ディスクの外観が悪化したり、ディスクに記録された
情報を読みとるための光が接着剤硬化物層で弱められる
ため読みとりに障害を生じる場合がある。したがって、
本発明の組成物を配合する場合には硬化物の光透過率が
上記範囲を満足するように各成分を配合することが望ま
しい。Further, it is desirable that the photocured product of the composition of the present invention is excellent in transparency, and for example, the light transmittance at 600 to 700 nm of a cured product having a thickness of 60 μm is usually 90% or more. . If the light transmittance is less than 90%, the appearance of the optical disk may be deteriorated, and the light for reading the information recorded on the disk may be weakened by the cured adhesive layer, which may cause a reading failure. Therefore,
When the composition of the present invention is blended, it is desirable to blend each component so that the light transmittance of the cured product satisfies the above range.
【0065】さらに、本発明の組成物の光硬化物の屈折
率は25℃で通常1.51〜1.70の範囲内になるよ
う各成分を配合することが望ましい。この範囲外である
とディスクに記録された情報を読みとるときに障害を生
じる場合がある。Further, it is desirable that the respective components are blended so that the refractive index of the photocured product of the composition of the present invention is usually in the range of 1.51 to 1.70 at 25 ° C. If it is out of this range, a trouble may occur when reading the information recorded on the disc.
【0066】本発明の組成物はポリカーボネート(P
C)やポリメタクリル酸メチル(PMMA)等のプラス
チック、金やアルミニウム等の金属、ガラス等の無機化
合物等に良好な接着力を示し、光ディスク用接着剤とし
て好適である。The composition of the present invention comprises polycarbonate (P
C) and polymethylmethacrylate (PMMA) and other plastics, metals such as gold and aluminum, inorganic compounds such as glass, etc. exhibit good adhesion and are suitable as an adhesive for optical disks.
【0067】[0067]
【0068】合成例1
攪拌機機、温度計を備えた1リットルのセパラブルフラ
スコに、イソホロンジイソシアネート209g、3,5
−ジ−t−ブチル−4−ヒドロキシトルエンを0.2
g、ジラウリル酸ジ−n−ブチルスズ0.8gを仕込み
攪拌し、乾燥空気雰囲気下で冷水浴で10℃に冷却した
後、内容物が10〜35℃に保たれるよう2−ヒドロキ
シエチルアクリレート109gを1時間かけて少量づつ
添加し反応させた。その後、水酸基価109.7mgK
OH/gのポリテトラメチレングリコール(商品名:P
TMG1000、三菱化学(株)製)480g添加し、
40〜60℃で5時間攪拌を継続し反応させた。その
後、反応物を取り出し数平均分子量が1650のウレタ
ンアクリレート(A1)を得た。 Synthesis Example 1 In a 1 liter separable flask equipped with a stirrer and a thermometer, 209 g of isophorone diisocyanate, 3,5
-Di-t-butyl-4-hydroxytoluene 0.2
g, 0.8 g of di-n-butyltin dilaurate was charged and stirred, and after cooling to 10 ° C. in a cold water bath under a dry air atmosphere, 109 g of 2-hydroxyethyl acrylate so that the contents were kept at 10 to 35 ° C. Was added little by little over 1 hour to react. Then, the hydroxyl value is 109.7 mgK
OH / g polytetramethylene glycol (trade name: P
480g of TMG1000, Mitsubishi Chemical Co., Ltd. was added,
Stirring was continued at 40 to 60 ° C. for 5 hours for reaction. Then, the reaction product was taken out to obtain a urethane acrylate (A1) having a number average molecular weight of 1650.
【0069】合成例2
合成例1のポリテトラメチレングリコールの代わりに水
酸基価111.7mgKOH/gのポリエステルジオー
ル(商品名:クラポールP1010、クラレ(株)製)
472g使用した以外は、合成例1と同様の操作を行
い、数平均分子量1530のウレタンアクリレート(A
2)を得た。 Synthesis Example 2 Instead of the polytetramethylene glycol of Synthesis Example 1, a polyester diol having a hydroxyl value of 111.7 mgKOH / g (trade name: Clapol P1010, manufactured by Kuraray Co., Ltd.)
The same operation as in Synthesis Example 1 was performed except that 472 g was used, and a urethane acrylate (A having a number average molecular weight of 1530) (A
2) was obtained.
【0070】合成例3
合成例1のポリテトラメチレングリコールの代わりに水
酸基価55.2mgKOH/gのポリエ−テルジオール
(商品名:PTG−L2000、保土谷化学工業(株)
製)956g使用した以外は、合成例1と同様の操作を
行い、数平均分子量2570のウレタンアクリレート
(A3)を得た。 Synthesis Example 3 Instead of the polytetramethylene glycol of Synthesis Example 1, a polyether diol having a hydroxyl value of 55.2 mgKOH / g (trade name: PTG-L2000, Hodogaya Chemical Co., Ltd.)
The same operation as in Synthesis Example 1 was performed except that 956 g of a urethane acrylate (A3) having a number average molecular weight of 2570 was obtained.
【0071】実施例および比較例
<放射硬化性塗膜形成用組成物の調製>撹拌機を備えた
反応容器に、表1に示す組成の各成分を加えた後、撹拌
混合して、実施例1〜3および比較例1〜4の塗膜用組
成物を調製した。表1における各成分は以下の通りであ
る。表中の成分の配合量は重量部である。
(B)成分
B1 4−ヒドロキシブチルアクリレート(市販品:4−HBA、大阪
有化学工業(株)製)
B2 2−ヒドロキシエチルアクリレート(市販品:HEA、大阪有機
化学工業(株)製)
(C)成分
C1 2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン(市
販品:Irgacure651、チバスペシャルティケミカルズ
(株)製)
C2 2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オ
ン(市販品:Darocur1173、チバスペシャルティケミ
カルズ(株)製)
(D)成分
D1 ヒドロキシピバリン酸ネオペンチルグリコールジアクリレート(
市販品:KAYARAD MANDA、日本化薬(株)製)
D2 フェノキシエチルアクリレート(市販品:ビスコート192、大
阪有機化学工業(株)製)
D3 ラウリルアクリレート(市販品:LA、大阪有機化学工業(株)
製)
D4 イソボルニルアクリレート(市販品:IBXA、大阪有機化学工
業(株)製)
D5 2−アクリロイルオキシプロピルハイドロゲンフタレート(市販
品: ビスコート2100、大阪有機化学工業(株)製)
D6 ノニルフェノールEO変性アクリレート(市販品:M111、東
亞合成(株)製)
D7 エトキシ化トリメチロールプロパントリアクリレート(市販品:
A−TMPT−3EO、新中村化学工業(株)製)
(E)成分
E1 2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェ
ニル)−ブタン−1−オン(市販品:Irgacure369、
チバスペシャルティケミカルズ(株)製)
E2 2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホ
リノ−プロパン−1−オン(市販品:Irgacure907、
チバスペシャルティケミカルズ(株)製)
E3 2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキ
シド(市販品:Lucirin TPO、BASF社製)
次に、上記のようにして調製された組成物(実施例1〜
2および比較例1〜4)を用いて、各組成物の、基材に
対する密着性、耐湿熱性を以下のようにして測定、評価
した。 Examples and Comparative Examples < Preparation of radiation-curable coating film-forming composition> To a reaction vessel equipped with a stirrer, the components having the compositions shown in Table 1 were added, and the mixture was stirred and mixed. The coating compositions of 1 to 3 and Comparative Examples 1 to 4 were prepared. Each component in Table 1 is as follows. The blending amounts of the components in the table are parts by weight. (B) Component B1 4-hydroxybutyl acrylate (commercial product: 4-HBA, manufactured by Osaka Yukagaku Kogyo Co., Ltd.) B2 2-hydroxyethyl acrylate (commercial product: HEA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) (C ) Component C1 2,2-dimethoxy-1,2-diphenylethan-1-one (commercially available product: Irgacure 651, manufactured by Ciba Specialty Chemicals Co., Ltd.) C2 2-hydroxy-2-methyl-1-phenyl-propane-1 -On (commercial product: Darocur1173, manufactured by Ciba Specialty Chemicals Co., Ltd.) (D) Component D1 hydroxypivalic acid neopentyl glycol diacrylate (commercial product: KAYARAD MANDA, manufactured by Nippon Kayaku Co., Ltd.) D2 phenoxyethyl acrylate (Commercial item: Viscoat 192, Osaka Organic Chemical Industry ( ) D3 lauryl acrylate (commercially available product: LA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) D4 isobornyl acrylate (commercially available product: IBXA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) D5 2-acryloyloxypropyl hydrogen phthalate (Commercial item: Viscoat 2100, manufactured by Osaka Organic Chemical Industry Co., Ltd.) D6 Nonylphenol EO modified acrylate (commercial item: M111, manufactured by Toagosei Co., Ltd.) D7 Ethoxylated trimethylolpropane triacrylate (commercial item: A-TMPT) -3EO, manufactured by Shin-Nakamura Chemical Co., Ltd. (E) Component E1 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one (commercially available product: Irgacure369, Ciba Specialty Chemicals) E2 2-methyl-1- [4- (methylthio) Phenyl] -2-morpholino-propan-1-one (commercial product: Irgacure 907, manufactured by Ciba Specialty Chemicals Co., Ltd.) E3 2,4,6-trimethylbenzoyldiphenylphosphine oxyside (commercial product: Lucirin TPO, BASF Corporation) Next, the composition prepared as described above (Examples 1 to 1)
2 and Comparative Examples 1 to 4), the adhesion and moist heat resistance of each composition to the substrate were measured and evaluated as follows.
【0072】基材に対する密着性
PC基板との接着性:PC基板(商品名:パンライト、
帝人化成(株)製)にスピンコーターにて前記組成物を
塗布し、光量100mJ/cm2 の光を窒素雰囲気下で
照射して膜厚50μmの前記組成物の硬化皮膜を得た。
該硬化皮膜にカッターナイフにて互いに中央で約90度
で交差する長さ1cmのクロスカット状に傷を付けた
後、セロテープをその上に張り付けた後に急激に該セロ
テープを引き剥がすクロスカットセロテープ剥離試験を
行った。該セロテープ剥離試験によって硬化皮膜が剥が
れる場合を接着性不良と判定し表1で×で表記した。ま
た、剥がれない場合を接着性良好と判定し表1で○で表
記した。Adhesion to base material Adhesion to PC substrate: PC substrate (trade name: Panlite,
The composition was applied to Teijin Kasei Co., Ltd. with a spin coater and irradiated with light having a light intensity of 100 mJ / cm 2 in a nitrogen atmosphere to obtain a cured film of the composition having a thickness of 50 μm.
Cross-cut cellophane tape peeling, in which the cured film was scratched in a cross-cut shape with a length of 1 cm intersecting each other at about 90 degrees at the center with a cutter knife, and then the cellophane tape was pasted thereon, and then the cellophane tape was rapidly peeled off. The test was conducted. When the cured film peeled off by the cellophane tape peeling test, it was judged that the adhesiveness was poor, and it was shown by x in Table 1. In addition, when it did not peel off, the adhesiveness was determined to be good, and the result is indicated by ◯ in Table 1.
【0073】アルミニウムとの接着性:上記PC基板上
にスパッタリング法により蒸着したアルミニウム皮膜に
スピンコーターにて前記組成物を塗布し、光量100m
J/cm2 の光を窒素雰囲気下で照射して膜厚50μm
の前記組成物の硬化皮膜を得た。前述のPC基板の場合
同様クロスカットセロテープ剥離試験を行い、アルミニ
ウム皮膜がPC基板から一部でも剥離が見られる場合を
接着性良好と判定し表1で○で表記した。また、剥がれ
ない場合を接着性不良と判定し表1で×で表記した。Adhesiveness to aluminum: The above composition was applied to an aluminum film deposited on the above-mentioned PC substrate by a sputtering method with a spin coater, and the light amount was 100 m.
Irradiate with J / cm 2 light under nitrogen atmosphere to obtain film thickness of 50 μm
A cured film of the above composition was obtained. A cross-cut cellophane tape peeling test was carried out in the same manner as in the case of the above-mentioned PC substrate, and a case where the aluminum film was partially peeled from the PC substrate was judged to be good in adhesiveness, and was marked with a circle in Table 1. In addition, when it did not peel off, it was determined that the adhesiveness was poor, and the result was marked with X in Table 1.
【0074】金との接着性:上記PC基板上にスパッタ
リング法により蒸着した金皮膜にスピンコーターにて前
記組成物を塗布し、光量100mJ/cm2 の光を窒素
雰囲気下で照射して膜厚50μmの前記組成物の硬化皮
膜を得た。前述のPC基板の場合同様クロスカットセロ
テープ剥離試験を行い、金皮膜がPC基板から一部でも
剥離が見られる場合を接着性良好と判定し表1で○で表
記した。また、剥がれない場合を接着性不良と判定し表
1で×で表記した。Adhesiveness to gold: The above composition was applied to a gold film deposited on the above-mentioned PC substrate by a sputtering method with a spin coater, and light having a light intensity of 100 mJ / cm 2 was irradiated in a nitrogen atmosphere to obtain a film thickness. A cured film of 50 μm of the composition was obtained. A cross-cut cellophane tape peeling test was carried out in the same manner as in the case of the above-mentioned PC substrate, and when the peeling of the gold film from the PC substrate was partially observed, the adhesiveness was judged to be good, and the result was marked with a circle in Table 1. In addition, when it did not peel off, it was determined that the adhesiveness was poor, and the result was marked with X in Table 1.
【0075】耐湿熱性
PC基板にスパッタリングして作製したアルミニウム基
板とPC基板、もしくはPC基板にスパッタリングして
作製したアルミニウム基板とPC基板にスパッタリング
して作製した金基板の組み合わせで塗膜厚が約50μm
になるようにスピンコーターにてはりあわせ、PC基板
側もしくはPC基板にスパッタリングして作製した金基
板側から光量500mJ/cm2 の光を照射して2枚の
基板を接着した。その後、温度90℃、相対湿度98%
RHの恒温恒湿槽に96時間放置した時に、接着剤層も
しくは接着剤と基板との界面に水泡、腐食等の異常が見
られた場合を耐湿熱性不良と判定し表1で×で表記し
た。また、異常が見られない場合を耐湿熱性良好と判定
し表1で○で表記した。A combination of an aluminum substrate and a PC substrate prepared by sputtering on a moisture and heat resistant PC substrate, or a combination of an aluminum substrate prepared by sputtering on a PC substrate and a gold substrate prepared by sputtering on a PC substrate has a coating film thickness of about 50 μm.
And the two substrates were adhered by irradiating with a spin coater so that the light intensity of 500 mJ / cm 2 was applied from the PC substrate side or the gold substrate side prepared by sputtering the PC substrate. After that, temperature 90 ℃, relative humidity 98%
When the adhesive layer or the interface between the adhesive and the substrate showed abnormalities such as water bubbles and corrosion when left in a thermo-hygrostat of RH for 96 hours, it was judged as poor moist-heat resistance and indicated by x in Table 1. . In addition, when no abnormality was observed, it was judged to be good in resistance to moist heat, and indicated by ◯ in Table 1.
【0076】上記の評価を行った結果について表1に示
す。この結果から、実施例1は(A)、(B)、
(C)、(D)、(E)全成分を含むものであり、すべ
ての評価項目、すなわちPC密着性、Al密着性、Au
密着性、耐湿熱性が優れていることが判る。実施例2で
は(D)成分、(E)成分を含まないが、(B)成分を
多めに含むものであり、特に耐湿熱性に優れていた。実
施例3は請求項3に対応した(E)成分を含まないもの
であるが、すべての評価項目において合格であった。一
方、本発明で必須な(B)成分、または/および(C)
成分を併用していない比較例1、2、3、4ではいずれ
も耐湿熱性が悪かった。また、一部のものではAl密着
性、Au密着性も悪かった。The results of the above evaluations are shown in Table 1. From these results, in Example 1, (A), (B),
(C), (D), (E) Contains all components, all evaluation items, namely PC adhesion, Al adhesion, Au
It can be seen that the adhesiveness and resistance to moist heat are excellent. In Example 2, the component (D) and the component (E) were not contained, but the component (B) was contained in a large amount, and the moisture and heat resistance was particularly excellent. Example 3 does not contain the component (E) corresponding to claim 3, but passed all the evaluation items. On the other hand, the component (B) and / or the component (C) which are essential in the present invention
In Comparative Examples 1, 2, 3, and 4, which did not use the components together, the wet heat resistance was poor. In addition, some of them had poor Al adhesion and Au adhesion.
【0077】[0077]
【表1】 [Table 1]
【0078】以上詳述した本発明の光ディスク用接着剤
の好ましい態様を以下に記する。
1.成分(A)のウレタン(メタ)アクリレートの数平
均分子量が600〜10000である光ディスク用接着
剤。
2.成分(A)と成分(B)と成分(C)の合計の重量
を100重量部として、成分(A)が5〜70重量部含
まれる光ディスク用接着剤。
3.成分(A)と成分(B)と成分(C)の合計の重量
を100重量部として、成分(B)が20〜90重量部
含まれる光ディスク用接着剤。
4.成分(A)と成分(B)と成分(C)の合計の重量
を100重量部として、成分(C)が1〜10重量部含
まれる光ディスク用接着剤。
5.成分(A)と成分(B)と成分(C)の合計の重量
を100重量部として、成分(A)が5〜70重量部、
成分(B)が20〜90重量部、成分(C)が1〜10
重量部であり、成分(D)は成分(B)の70重量%以
下で成分(B)の代替として含まれ、成分(E)は成分
(C)の70重量%以下で成分(C)の代替として含ま
れる光ディスク用接着剤
25℃での粘度が150〜2000mPa・sである光
ディスク用接着剤。
6.組成物に紫外線を照射して得られる硬化物のガラス
転移温度が0〜120℃である光ディスク用接着剤。
7.組成物に紫外線を照射して得られる硬化物の25℃
における屈折率が1.51〜1.70である光ディスク
用接着剤。Preferred embodiments of the optical disk adhesive of the present invention detailed above will be described below. 1. An adhesive for optical disks, wherein the urethane (meth) acrylate of component (A) has a number average molecular weight of 600 to 10,000. 2. An adhesive agent for an optical disc, which contains 5 to 70 parts by weight of the component (A), with the total weight of the component (A), the component (B) and the component (C) being 100 parts by weight. 3. An adhesive for optical disks, wherein the total weight of the component (A), the component (B) and the component (C) is 100 parts by weight, and the component (B) is contained in an amount of 20 to 90 parts by weight. 4. An adhesive agent for optical disks, which contains 1 to 10 parts by weight of the component (C), with the total weight of the component (A), the component (B) and the component (C) being 100 parts by weight. 5. Assuming that the total weight of the component (A), the component (B) and the component (C) is 100 parts by weight, the component (A) is 5 to 70 parts by weight,
20-90 parts by weight of component (B), 1-10 of component (C)
Parts by weight, the component (D) is contained as an alternative to the component (B) in 70% by weight or less of the component (B), and the component (E) is contained as 70% by weight or less of the component (C) in the component (C). Optical disk adhesive included as an alternative An optical disk adhesive having a viscosity of 150 to 2000 mPa · s at 25 ° C. 6. An adhesive agent for optical disks, wherein the cured product obtained by irradiating the composition with ultraviolet rays has a glass transition temperature of 0 to 120 ° C. 7. 25 ° C. of a cured product obtained by irradiating the composition with ultraviolet rays
An optical disk adhesive having a refractive index of 1.51 to 1.70.
【0079】[0079]
【発明の効果】以上説明したように、本発明の光ディス
ク用接着剤は、速硬化性、高い光透過性、ディスクを構
成する樹脂、反射膜、半透過膜などとの良好な接着性を
保持した上で、優れた耐湿熱性を有しているので、光デ
ィスクの製造に於いて従来の接着剤と比較して極めて有
用である。As described above, the adhesive for an optical disk of the present invention has fast curing property, high light transmittance, and good adhesiveness with the resin, the reflective film, the semi-transmissive film, and the like that compose the disk. In addition, since it has excellent resistance to moisture and heat, it is extremely useful in the manufacture of optical disks as compared with conventional adhesives.
フロントページの続き (72)発明者 高橋 俊彦 東京都中央区築地二丁目11番24号 ジェイ エスアール株式会社内 (72)発明者 宇加地 孝志 東京都中央区築地二丁目11番24号 ジェイ エスアール株式会社内 Fターム(参考) 4J040 FA141 FA142 FA151 FA152 FA211 FA212 FA271 FA272 FA291 FA292 GA02 HB19 JB08 KA13 LA01 LA06 LA07 LA08 MA02 MA10 NA17 NA21 5D029 RA30 Continued front page (72) Inventor Toshihiko Takahashi 2-11-21 Tsukiji, Chuo-ku, Tokyo J Within SRL Co., Ltd. (72) Inventor Takashi Ukaji 2-11-21 Tsukiji, Chuo-ku, Tokyo J Within SRL Co., Ltd. F term (reference) 4J040 FA141 FA142 FA151 FA152 FA211 FA212 FA271 FA272 FA291 FA292 GA02 HB19 JB08 KA13 LA01 LA06 LA07 LA08 MA02 MA10 NA17 NA21 5D029 RA30
Claims (4)
(A)ポリオール化合物、ポリイソシアネート化合物お
よび水酸基含有(メタ)アクリレート化合物を反応させ
て得られるウレタン(メタ)アクリレート、(B)ヒド
ロキシアルキル(メタ)アクリレート、(C)2,2−
ジメトキシ−1,2−ジフェニルエタン−1−オン、2
−ヒドロキシ−2−メチル−1−フェニル−プロパン−
1−オンおよび/または1−ヒドロキシ−シクロヘキシ
ルフェニルケトンを含有する光ディスク用接着剤。1. The following components (A), (B) and (C):
(A) a polyol compound, a polyisocyanate compound, and a urethane (meth) acrylate obtained by reacting a hydroxyl group-containing (meth) acrylate compound, (B) a hydroxyalkyl (meth) acrylate, (C) 2,2-
Dimethoxy-1,2-diphenylethan-1-one, 2
-Hydroxy-2-methyl-1-phenyl-propane-
An adhesive for optical disks, which contains 1-one and / or 1-hydroxy-cyclohexyl phenyl ketone.
タ)アクリレートである請求項1記載の光ディスク用接
着剤。2. The adhesive for optical disks according to claim 1, wherein the component (B) is 4-hydroxybutyl (meth) acrylate.
(B)成分以外の単官能性および/または多官能性(メ
タ)アクリレートを含有する請求項1または2記載の光
ディスク用接着剤。3. The adhesive for an optical disk according to claim 1, further comprising (D) a monofunctional and / or polyfunctional (meth) acrylate other than the components (A) and (B).
重合開始剤を含有する請求項1〜3のいずれか1項記載
の光ディスク用接着剤。4. The adhesive for optical disks according to claim 1, which further comprises (E) a photopolymerization initiator other than the component (C).
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23399798A JP3988267B2 (en) | 1998-08-20 | 1998-08-20 | Adhesive for optical disc |
EP99925458A EP1112330B1 (en) | 1998-08-20 | 1999-05-21 | Adhesive for optical disks |
CNB998123978A CN1160431C (en) | 1998-08-20 | 1999-05-21 | Adhesive for optical disks |
PCT/NL1999/000322 WO2000011097A1 (en) | 1998-08-20 | 1999-05-21 | Adhesive for optical disks |
DE69924506T DE69924506T2 (en) | 1998-08-20 | 1999-05-21 | Adhesives for optical discs |
KR1020017002176A KR100600254B1 (en) | 1998-08-20 | 1999-05-21 | Adhesive for optical disks |
TW088108762A TWI222460B (en) | 1998-08-20 | 1999-05-27 | Adhesive for optical disks |
US09/357,276 US6337118B1 (en) | 1998-08-20 | 1999-07-20 | Adhesive for optical disks |
HK02103686.1A HK1042106B (en) | 1998-08-20 | 2002-05-15 | Adhesive for optical disks |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23399798A JP3988267B2 (en) | 1998-08-20 | 1998-08-20 | Adhesive for optical disc |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2000063766A true JP2000063766A (en) | 2000-02-29 |
JP3988267B2 JP3988267B2 (en) | 2007-10-10 |
Family
ID=16963943
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP23399798A Expired - Lifetime JP3988267B2 (en) | 1998-08-20 | 1998-08-20 | Adhesive for optical disc |
Country Status (4)
Country | Link |
---|---|
US (1) | US6337118B1 (en) |
JP (1) | JP3988267B2 (en) |
KR (1) | KR100600254B1 (en) |
TW (1) | TWI222460B (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002129113A (en) * | 2000-08-15 | 2002-05-09 | Jsr Corp | Adhesive composition for optical disc |
JP2002265885A (en) * | 2001-03-15 | 2002-09-18 | Nippon Kayaku Co Ltd | Adhesive composition for optical disk, cured product, and article therefrom |
WO2003072625A1 (en) * | 2002-02-28 | 2003-09-04 | Luvantix Co., Ltd. | Photocurable resin composition for optical waveguide and optical waveguide made of the same |
US6818681B2 (en) | 2002-02-22 | 2004-11-16 | Nagase Chemtex Corporation | Ultraviolet-curable resin composition for optical discs |
JP2006348230A (en) * | 2005-06-17 | 2006-12-28 | Jsr Corp | Ultraviolet ray-curable liquid composition for adhesive and adhesive |
WO2007026631A1 (en) * | 2005-08-31 | 2007-03-08 | Sanyo Chemical Industries, Ltd. | Adhesive for shaped article production, adhesive composition and shaped article using those |
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CN102234360B (en) * | 2010-04-23 | 2014-08-27 | 东友精细化工有限公司 | Resin-type lightguide plate composition, backlight unit, and liquid crystal display |
CN103031064A (en) * | 2011-09-30 | 2013-04-10 | 三星电机株式会社 | Adhesive resin composition for HDD motor and HDD motor fabricated by using the same |
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JP2020517764A (en) * | 2017-04-26 | 2020-06-18 | エシロール・アンテルナシオナル | Optical adhesive for glass and polycarbonate |
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Also Published As
Publication number | Publication date |
---|---|
TWI222460B (en) | 2004-10-21 |
JP3988267B2 (en) | 2007-10-10 |
KR100600254B1 (en) | 2006-07-13 |
US6337118B1 (en) | 2002-01-08 |
KR20010072808A (en) | 2001-07-31 |
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